JPH0552824B2 - - Google Patents

Info

Publication number: JPH0552824B2
Authority: JP; Japan
Prior art keywords: group; formula; reaction; general formula; mmol
Prior art date: 1990-02-13
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

JP2032214A

Other languages

English (en)

Japanese (ja)

Other versions

JPH03236369A (ja

Inventor

Katsumi Yonemoto

Isao Shibuya

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

National Institute of Advanced Industrial Science and Technology AIST

Original Assignee

Agency of Industrial Science and Technology

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.)

1990-02-13

Filing date

1990-02-13

Publication date

1993-08-06

1990-02-13 Application filed by Agency of Industrial Science and Technology filed Critical Agency of Industrial Science and Technology

1990-02-13 Priority to JP2032214A priority Critical patent/JPH03236369A/ja

1991-10-22 Publication of JPH03236369A publication Critical patent/JPH03236369A/ja

1993-08-06 Publication of JPH0552824B2 publication Critical patent/JPH0552824B2/ja

Status Granted legal-status Critical Current

Links

QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical class [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
229910000104 sodium hydride Inorganic materials 0.000 claims description 7
239000012312 sodium hydride Substances 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 6
239000012990 dithiocarbamate Substances 0.000 claims description 6
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
-1 p-anisyl group Chemical group 0.000 description 10
238000000034 method Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
239000011630 iodine Substances 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
239000002994 raw material Substances 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
MNNJLAZJQBWSST-UHFFFAOYSA-N 1,4,2-dithiazole Chemical class C1SC=NS1 MNNJLAZJQBWSST-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
XQIJUNRYEIASNK-UHFFFAOYSA-N amino carbamodithioate Chemical class NSC(N)=S XQIJUNRYEIASNK-UHFFFAOYSA-N 0.000 description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000012053 oil suspension Substances 0.000 description 2
NSVHDIYWJVLAGH-UHFFFAOYSA-M silver;n,n-diethylcarbamodithioate Chemical compound [Ag+].CCN(CC)C([S-])=S NSVHDIYWJVLAGH-UHFFFAOYSA-M 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
BTBUDFIPZVFTDQ-UHFFFAOYSA-N benzamido n,n-diethylcarbamodithioate Chemical compound CCN(CC)C(=S)SNC(=O)C1=CC=CC=C1 BTBUDFIPZVFTDQ-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000006210 cyclodehydration reaction Methods 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960003966 nicotinamide Drugs 0.000 description 1
235000005152 nicotinamide Nutrition 0.000 description 1
239000011570 nicotinamide Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1

JP2032214A 1990-02-13 1990-02-13 スルフェンアミド誘導体の製造方法 Granted JPH03236369A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP2032214A JPH03236369A (ja)	1990-02-13	1990-02-13	スルフェンアミド誘導体の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2032214A JPH03236369A (ja)	1990-02-13	1990-02-13	スルフェンアミド誘導体の製造方法

Publications (2)

Publication Number	Publication Date
JPH03236369A JPH03236369A (ja)	1991-10-22
JPH0552824B2 true JPH0552824B2 (ru)	1993-08-06

Family

ID=12352675

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2032214A Granted JPH03236369A (ja)	1990-02-13	1990-02-13	スルフェンアミド誘導体の製造方法

Country Status (1)

Country	Link
JP (1)	JPH03236369A (ru)

1990
- 1990-02-13 JP JP2032214A patent/JPH03236369A/ja active Granted

Also Published As

Publication number	Publication date
JPH03236369A (ja)	1991-10-22

Legal Events

Date	Code	Title	Description
2010-02-13	EXPY	Cancellation because of completion of term

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JPH0552824B2 (ru)	1993-08-06
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