CS209943B2 - Method of making the 5-mescaptol-1,2,3-triazoles - Google Patents

Method of making the 5-mescaptol-1,2,3-triazoles Download PDF

Info

Publication number: CS209943B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; reaction; thiadiazole; azide; phenol
Prior art date: 1978-11-29

Application number

CS798246A

Other languages

Czech (cs)

English (en)

Inventor

Hans-Rudolf Krueger

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-11-29

Filing date

1979-11-29

Publication date

1981-12-31

1979-11-29 Application filed by Schering Ag filed Critical Schering Ag

1981-12-31 Publication of CS209943B2 publication Critical patent/CS209943B2/cs

Links

238000004519 manufacturing process Methods 0.000 title description 10
238000000034 method Methods 0.000 claims abstract description 22
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 8
238000006555 catalytic reaction Methods 0.000 claims abstract description 7
-1 pentachlorophenyl Chemical group 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 14
LLCOQBODWBFTDD-UHFFFAOYSA-N 1h-triazol-1-ium-4-thiolate Chemical class SC1=CNN=N1 LLCOQBODWBFTDD-UHFFFAOYSA-N 0.000 claims description 13
150000001540 azides Chemical class 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 7
UDSVLKOSDHNDNJ-UHFFFAOYSA-N thiadiazole-5-carbonyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CN=NS1 UDSVLKOSDHNDNJ-UHFFFAOYSA-N 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
IZBAXOUZLXYCRJ-UHFFFAOYSA-N thiadiazol-4-ylcarbamic acid Chemical compound OC(=O)NC1=CSN=N1 IZBAXOUZLXYCRJ-UHFFFAOYSA-N 0.000 claims 1
RIQQSJALVAEHSB-UHFFFAOYSA-N thiadiazol-5-yl hydrogen carbonate Chemical compound OC(=O)OC1=CN=NS1 RIQQSJALVAEHSB-UHFFFAOYSA-N 0.000 claims 1
ZGJIPMGEIQGQID-UHFFFAOYSA-N thiadiazole-4-carbonyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CSN=N1 ZGJIPMGEIQGQID-UHFFFAOYSA-N 0.000 claims 1
239000003960 organic solvent Substances 0.000 abstract description 5
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
PVGHNTXQMCYYGF-UHFFFAOYSA-N thiadiazol-5-amine Chemical compound NC1=CN=NS1 PVGHNTXQMCYYGF-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000000203 mixture Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002585 base Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000003513 alkali Substances 0.000 description 5
239000012045 crude solution Substances 0.000 description 5
239000002024 ethyl acetate extract Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000007858 starting material Substances 0.000 description 5
MMVXXBHGORJZQP-UHFFFAOYSA-N thiadiazol-5-ylcarbamic acid Chemical compound OC(=O)NC1=CN=NS1 MMVXXBHGORJZQP-UHFFFAOYSA-N 0.000 description 5
FKDUPDCCGBMNPT-UHFFFAOYSA-N 4-methyl-1,2-dihydrotriazole-5-thione Chemical compound CC=1N=NNC=1S FKDUPDCCGBMNPT-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000006731 degradation reaction Methods 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
150000001731 carboxylic acid azides Chemical class 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DHTBORBAEQJWLZ-UHFFFAOYSA-N thiadiazole-5-carbohydrazide Chemical class NNC(=O)C1=CN=NS1 DHTBORBAEQJWLZ-UHFFFAOYSA-N 0.000 description 3
BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical group OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 description 2
HXABWNOBBYCXLG-UHFFFAOYSA-N 5-isocyanatothiadiazole Chemical compound O=C=NC1=CN=NS1 HXABWNOBBYCXLG-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
238000006088 Dimroth rearrangement reaction Methods 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
150000007529 inorganic bases Chemical group 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
239000004476 plant protection product Substances 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
XXYDUYVNVIQPBE-UHFFFAOYSA-N 2h-1,2-thiazole-5-thione Chemical compound S=C1C=CNS1 XXYDUYVNVIQPBE-UHFFFAOYSA-N 0.000 description 1
QFCSRTHGBBTPLC-UHFFFAOYSA-N 2h-thiadiazole-5-thione Chemical compound S=C1C=NNS1 QFCSRTHGBBTPLC-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
OIZCCHUUSZFPIW-UHFFFAOYSA-N 4-methylthiadiazole-5-carbohydrazide Chemical compound CC=1N=NSC=1C(=O)NN OIZCCHUUSZFPIW-UHFFFAOYSA-N 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KZXIQMSWVSTGQX-UHFFFAOYSA-N SC1=CN=NS1 Chemical class SC1=CN=NS1 KZXIQMSWVSTGQX-UHFFFAOYSA-N 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
JNFRPHKXOCFXJF-UHFFFAOYSA-N azide Chemical class [N-]=[N+]=[N-].[N-]=[N+]=[N-] JNFRPHKXOCFXJF-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000002641 lithium Chemical group 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000010959 steel Substances 0.000 description 1
GAEVUCDHQSJZEB-UHFFFAOYSA-N tert-butyl n-(4-methylthiadiazol-5-yl)carbamate Chemical compound CC=1N=NSC=1NC(=O)OC(C)(C)C GAEVUCDHQSJZEB-UHFFFAOYSA-N 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
ARCYBHORWYHDNX-UHFFFAOYSA-N thiadiazol-5-yl carbamate Chemical compound NC(=O)OC1=CN=NS1 ARCYBHORWYHDNX-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000003466 welding Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS798246A 1978-11-29 1979-11-29 Method of making the 5-mescaptol-1,2,3-triazoles CS209943B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782852067 DE2852067A1 (de)	1978-11-29	1978-11-29	Verfahren zur herstellung von 5-mercapto-1,2,3-triazolen

Publications (1)

Publication Number	Publication Date
CS209943B2 true CS209943B2 (en)	1981-12-31

Family

ID=6056090

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS798246A CS209943B2 (en)	1978-11-29	1979-11-29	Method of making the 5-mescaptol-1,2,3-triazoles

Country Status (35)

Country	Link
US (1)	US4259502A (de)
JP (1)	JPS5919942B2 (de)
AR (1)	AR223689A1 (de)
AT (1)	AT371452B (de)
AU (1)	AU532061B2 (de)
BE (1)	BE880340A (de)
BR (1)	BR7907704A (de)
CA (1)	CA1137495A (de)
CH (1)	CH642362A5 (de)
CS (1)	CS209943B2 (de)
DD (1)	DD149521A5 (de)
DE (1)	DE2852067A1 (de)
DK (1)	DK508579A (de)
EG (1)	EG14014A (de)
ES (1)	ES486377A1 (de)
FI (1)	FI66363C (de)
FR (1)	FR2442838A1 (de)
GB (1)	GB2038328B (de)
GR (1)	GR74142B (de)
HU (1)	HU183023B (de)
IE (1)	IE49120B1 (de)
IL (1)	IL58796A0 (de)
IT (1)	IT1127268B (de)
LU (1)	LU81925A1 (de)
MX (1)	MX6016E (de)
NL (1)	NL7908605A (de)
NZ (1)	NZ192180A (de)
PH (1)	PH15774A (de)
PL (1)	PL120299B1 (de)
PT (1)	PT70497A (de)
RO (1)	RO78488A (de)
SE (1)	SE445997B (de)
SU (1)	SU961559A3 (de)
YU (1)	YU41352B (de)
ZA (1)	ZA796479B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2920939A1 (de) *	1979-05-21	1980-11-27	Schering Ag	Verfahren zur herstellung von 5-mercapto-1,2,3-triazolen
DE3139506A1 (de) *	1981-10-01	1983-04-21	Schering Ag, 1000 Berlin Und 4619 Bergkamen	1,2,3-thiadiazol-5-yl-harnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wuchsregulatorischer und entblaetternder wirkung
US5068347A (en) *	1987-11-23	1991-11-26	Dowelanco	Process for the preparation of 3-mercapto-5-amino-(1h)-1,2,4-triazole

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1476981A (en) *	1974-06-05	1977-06-16	Bristol Myers Co	Substituted penicillanic acids

1978
- 1978-11-29 DE DE19782852067 patent/DE2852067A1/de not_active Withdrawn
1979
- 1979-11-12 FI FI793526A patent/FI66363C/fi not_active IP Right Cessation
- 1979-11-19 YU YU2821/79A patent/YU41352B/xx unknown
- 1979-11-21 US US06/096,574 patent/US4259502A/en not_active Expired - Lifetime
- 1979-11-21 NZ NZ192180A patent/NZ192180A/xx unknown
- 1979-11-23 SE SE7909709A patent/SE445997B/sv unknown
- 1979-11-25 IL IL58796A patent/IL58796A0/xx unknown
- 1979-11-26 LU LU81925A patent/LU81925A1/de unknown
- 1979-11-26 MX MX798498U patent/MX6016E/es unknown
- 1979-11-26 PT PT70497A patent/PT70497A/de unknown
- 1979-11-27 EG EG707/79A patent/EG14014A/xx active
- 1979-11-27 GR GR60618A patent/GR74142B/el unknown
- 1979-11-27 PH PH23335A patent/PH15774A/en unknown
- 1979-11-27 PL PL1979219913A patent/PL120299B1/pl unknown
- 1979-11-27 IT IT27581/79A patent/IT1127268B/it active
- 1979-11-27 ES ES486377A patent/ES486377A1/es not_active Expired
- 1979-11-27 NL NL7908605A patent/NL7908605A/nl not_active Application Discontinuation
- 1979-11-28 AT AT0753579A patent/AT371452B/de not_active IP Right Cessation
- 1979-11-28 AU AU53242/79A patent/AU532061B2/en not_active Ceased
- 1979-11-28 DD DD79217206A patent/DD149521A5/de unknown
- 1979-11-28 HU HU79SCHE703A patent/HU183023B/hu unknown
- 1979-11-28 CA CA000340758A patent/CA1137495A/en not_active Expired
- 1979-11-28 BR BR7907704A patent/BR7907704A/pt unknown
- 1979-11-28 SU SU792845868A patent/SU961559A3/ru active
- 1979-11-29 JP JP54153696A patent/JPS5919942B2/ja not_active Expired
- 1979-11-29 AR AR279068A patent/AR223689A1/es active
- 1979-11-29 BE BE0/198355A patent/BE880340A/fr not_active IP Right Cessation
- 1979-11-29 CH CH1062679A patent/CH642362A5/de not_active IP Right Cessation
- 1979-11-29 FR FR7929392A patent/FR2442838A1/fr active Granted
- 1979-11-29 RO RO7999390A patent/RO78488A/ro unknown
- 1979-11-29 ZA ZA00796479A patent/ZA796479B/xx unknown
- 1979-11-29 CS CS798246A patent/CS209943B2/cs unknown
- 1979-11-29 IE IE2291/79A patent/IE49120B1/en unknown
- 1979-11-29 GB GB7941230A patent/GB2038328B/en not_active Expired
- 1979-11-29 DK DK508579A patent/DK508579A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
GB2038328B (en)	1983-03-23
PL219913A1 (de)	1980-12-01
AR223689A1 (es)	1981-09-15
EG14014A (en)	1982-09-30
FR2442838A1 (fr)	1980-06-27
SU961559A3 (ru)	1982-09-23
AU532061B2 (en)	1983-09-15
IL58796A0 (en)	1980-02-29
ES486377A1 (es)	1980-05-16
YU282179A (en)	1983-02-28
FR2442838B1 (de)	1983-10-21
ATA753579A (de)	1982-11-15
IT1127268B (it)	1986-05-21
AU5324279A (en)	1980-06-26
IE49120B1 (en)	1985-08-07
IT7927581A0 (it)	1979-11-27
FI793526A (fi)	1980-05-30
US4259502A (en)	1981-03-31
IE792291L (en)	1980-05-29
LU81925A1 (de)	1980-02-29
PL120299B1 (en)	1982-02-27
RO78488A (ro)	1982-02-26
BE880340A (fr)	1980-05-29
DD149521A5 (de)	1981-07-15
AT371452B (de)	1983-06-27
ZA796479B (en)	1980-11-26
GB2038328A (en)	1980-07-23
GR74142B (de)	1984-06-06
BR7907704A (pt)	1980-07-22
PH15774A (en)	1983-03-24
HU183023B (en)	1984-04-28
FI66363C (fi)	1984-10-10
MX6016E (es)	1984-09-24
FI66363B (fi)	1984-06-29
NL7908605A (nl)	1980-06-02
SE445997B (sv)	1986-08-04
SE7909709L (sv)	1980-05-30
JPS5919942B2 (ja)	1984-05-09
DK508579A (da)	1980-05-30
DE2852067A1 (de)	1980-06-12
CA1137495A (en)	1982-12-14
YU41352B (en)	1987-02-28
NZ192180A (en)	1982-11-23
PT70497A (de)	1979-12-01
CH642362A5 (de)	1984-04-13
JPS5573664A (en)	1980-06-03

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KR920010393B1 (ko)	1992-11-27	헤테로아릴옥시아세트아미드의 제조방법
CS209943B2 (en)	1981-12-31	Method of making the 5-mescaptol-1,2,3-triazoles
JP5087609B2 (ja)	2012-12-05	ハロゲン化２−（３−ブテニルスルファニル）−１，３−チアゾールを製造する方法
JPS5826913B2 (ja)	1983-06-06	１，２，３−チアジアゾ−ル−５−イル−尿素の製造法
US3992444A (en)	1976-11-16	Production of sulfamic acid halides
SU1241991A3 (ru)	1986-06-30	Способ получени 5-меркапто-1,2,3-триазолов
KR100674098B1 (ko)	2007-01-26	Ｎ,ｎ-디알킬아릴아민 촉매의 존재하에서ｎ-알크(엔)옥시(또는 아릴옥시)카보닐이소티오시아네이트 및 그의 유도체를 제조하는 방법
US4391979A (en)	1983-07-05	Process for the preparation of (2-amino-thiazol-4yl)-acetic acid hydrochloride
EP0131472B1 (de)	1989-03-22	5-Mercapto-1,2,3-thiadiazol-Zusammensetzungen und Verfahren zu deren Herstellung
US5633387A (en)	1997-05-27	Process for producing 1-(2-chlorophenyl)-5(4H)-tetrazolinone
US3669982A (en)	1972-06-13	Method for preparing 1,3,4-thiadiazole-2-ylureas
CS209936B2 (en)	1981-12-31	Method of making the 1,2,3-thiazoazol-5-ylureas
KR840000240B1 (ko)	1984-03-07	5-메르캅토-1,2,3-트리아졸의 제조방법
US4721782A (en)	1988-01-26	Method of preparing hydrazine-thiocarboxylic acid o-carbamoylmethyl esters
JPS6244545B2 (de)	1987-09-21
UA51621C2 (uk)	2002-12-16	Похідні 3-аміно-2-меркаптобензойної кислоти та способи їх одержання
CS196390B2 (cs)	1980-03-31	Způsob přípravy esterů thiokarbamové kyseliny