GB538822A - Manufacture of amidine derivatives - Google Patents
Manufacture of amidine derivativesInfo
- Publication number
- GB538822A GB538822A GB2065/40A GB206540A GB538822A GB 538822 A GB538822 A GB 538822A GB 2065/40 A GB2065/40 A GB 2065/40A GB 206540 A GB206540 A GB 206540A GB 538822 A GB538822 A GB 538822A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- reacted
- reduced
- chloride
- aminobenzenesulphon
- Prior art date
- 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
Links
- 150000001409 amidines Chemical class 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 18
- -1 heterocyclic amine Chemical class 0.000 abstract 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 10
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 10
- 229910021529 ammonia Inorganic materials 0.000 abstract 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 6
- QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 4
- 125000004442 acylamino group Chemical group 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- 150000001412 amines Chemical class 0.000 abstract 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 3
- 150000004820 halides Chemical class 0.000 abstract 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- IBDVYGIGYPWWBX-WCBMZHEXSA-N (1r,3s)-1-methyl-3-propan-2-ylcyclopentane-1-carboxylic acid Chemical compound CC(C)[C@H]1CC[C@@](C)(C(O)=O)C1 IBDVYGIGYPWWBX-WCBMZHEXSA-N 0.000 abstract 2
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 abstract 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 abstract 2
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 abstract 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 238000006467 substitution reaction Methods 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- 150000003456 sulfonamides Chemical class 0.000 abstract 2
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical class CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 abstract 1
- REHQLKUNRPCYEW-UHFFFAOYSA-N 1-methylcyclohexane-1-carboxylic acid Chemical class OC(=O)C1(C)CCCCC1 REHQLKUNRPCYEW-UHFFFAOYSA-N 0.000 abstract 1
- XMDBJQOQTPRRJM-UHFFFAOYSA-N 1-nitro-n-oxido-n-oxomethanimidamide Chemical compound NC(=N)[N+]([O-])=O XMDBJQOQTPRRJM-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 abstract 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 abstract 1
- DAUAQNGYDSHRET-UHFFFAOYSA-N 3,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1OC DAUAQNGYDSHRET-UHFFFAOYSA-N 0.000 abstract 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 abstract 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 abstract 1
- NMTLPEBBGGPJQP-UHFFFAOYSA-N 4,5-dimethyl-1,3-oxazole-2-carboxylic acid Chemical class CC=1N=C(C(O)=O)OC=1C NMTLPEBBGGPJQP-UHFFFAOYSA-N 0.000 abstract 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical class OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 abstract 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 abstract 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 abstract 1
- DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical class COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005639 Lauric acid Substances 0.000 abstract 1
- GPVDHNVGGIAOQT-UHFFFAOYSA-N Veratric acid Natural products COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001253 acrylic acids Chemical class 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 abstract 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- QLACLEPYLWLNTD-UHFFFAOYSA-N dihydrocinnamic acid Natural products COc1ccc(CCC(O)=O)c(O)c1OC QLACLEPYLWLNTD-UHFFFAOYSA-N 0.000 abstract 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 abstract 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 abstract 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- NKQBQVNKUQULLD-UHFFFAOYSA-N n'-methylethanimidamide Chemical compound CNC(C)=N NKQBQVNKUQULLD-UHFFFAOYSA-N 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 abstract 1
- 229940080818 propionamide Drugs 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract 1
- 238000011282 treatment Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
538,822. Sulphonamide derivatives. GEIGY AKT.-GES, J. R. Feb. 2, 1940, No. 2065. Convention date, Dec. 19, 1939. Samples furnished. [Class 2 (iii)] Sulphonamide derivatives or amidines of the general formula R,-SO 2 -N =C-N | R 2 #<SP>R3</SP> R4 are prepared by reacting an imido halide of the general formula R 1 -SO 2 -N =C-R 2 Hal with ammonia, a primary or secondary aliphatic or hydroaromatic amine, or a primary araliphatic, aromatic or heterocyclic amine. In the above formula R, represents a benzene nucleus containing in the para position a nitro group or an acylamino group R is a substituted or unsubstituted saturated or unsaturated residue of the aliphatic, alicyclic, araliphatic, aromatic, hydroaromatic, or heterocyclic series. R 3 and R 4 represent hydrogen or substituted or unsubstituted aliphatic, araliphatic, aromatic, hydroaromatic or heterocyclic residues which in some cases may be linked to one another. The desired compounds may also be obtained bv causing an amidine of the formula HN =C-R 2 | R 3 -N-R 4 where R 2 2, R and R 4 have the meanings given above to react with a benzene sulphonic acid halide having in the para position a nitro group or an acylamino group. The parent imido halides may be made by treating a benzene sulphonacylamide substituted in the para position by a nitro group on an acylamino group with an acid halide, particularly with a chloride of carbonic acid or sulphuric or the phosphorus acids. For the acyl residue there are mentioned the residues of aliphatic mono-, and di-carboxylic acids such as acetic, chloracetic, and alkoxyacetic acids, propionic acid, butyric acid, caproic acid, lauric acid, succinic acid or di-alkyl-oxamic acid ; also saturated or unsaturated substituted or unsubstituded araliphatic carboxylic acids such as phenylacetic acids, p-chlor-phenylacetic, and methoxyphenyl-acetic acids, dihydrocinnamic acid and phenoxyacetic acid ; also substituted or unsubstituted aromatic mono-, or di-carboxylic acids such as benzoic acid or its substitution products such as p-nitro-, and p-chlorobenzoic acids ; also alicyclic carboxylic acids such as fencholic acid or naphthenic acid ; also hydroaromatic acids such as hexahydrobenzoic and methylhexahydrobenzoic acids ; also hetrocyclic acids such as furane-2-carboxylic acid, pyridine carboxylic acid and amines mentioned as suitable for the process of the present invention include methylamine, ethylamine, propylamine, isopropylamine, alkylamine, butylamine, dimethylamine, diethylamine, dialkylamine, dipropylamine, methylpropylamine, aminoethanols, laurylamine, aniline and its substitution products such as anisidine or phenetidine, also piperidine, benzylamine, cyclohexylamine, pipecoline, and lupetidine. The reaction of the amine with the imino halide may take place either directly or in the presence of an inert solvent. In examples (1) Paranitrobenzene sulphonasetamide is treated with phosphorus pentachloride and the imido chloride so produced reacted with dry ammonia to give p-nitrophenyl sulphonamidine which on reduction by catalytic hydrogenation gives N-(p-amino-benzenesulphon)-acetamine ; (2) Acetamidine hydrochloride is treated with para-nitrobenzene sulphonic acid chloride in suspension in dry pyridine and the nitrocompound so produced is reduced to give the same amidine as in example (1) ; (3) A benzene solution of para-nitrobenzenesulphonacetamido chloride is shaken with aqueous methylamine, and the product reduced catalytically to give N-(p-aminobenzenesulphon)-N<SP>1</SP>-methyl - aceta - midine. The same compound is obtained by condensation of N-methyl-acetamidine with p-nitrobenzenesulphonic acid chloride and reduction; (4) The imido chloride of example (1) is reacted with ethylamine and then reduced to N -(p-aminobenzenesulphon)- N<SP>1</SP>-ethyl acetamidine propylamine may be used instead of ethylamine ; (5) The imido chloride of pnitrobenzenesulphonacetamide is reacted with diethylamine and reduced to N-(p-aminobenzenesulphon)-N<SP>1</SP>-diethylacetamidine; (6) Dialikylamine is substituted for diethylamine in example (5) ; (7) Ethanolamine is reacted with p-nitrobenzenesulphonacetamido chloride and reduced ; (8) monoalkylamine is substituted for monomethylamine. The product may be hydrogenated to produce a saturated compound; (9) Piperidine is reacted with p-nitrobenzenesulphon-acetimido chloride and reduced. Pipecoline, lupetidine or morpholine may be substituted for pyridine ; (10) p-nitrobenzenesulphon-propionamide is reacted with phosphorus chloride and the products treated with ammonia and reduced to N-(p-aminobenzenesulphbn)-propionamidine. The ammonia may be replaced by aliphatic amines; (11) pnitrobenzenesulphonbenzamide is reacted with phosphorus pentachloride, reacted with ammonia and reduced to N (p-aminobenzenesulphon) benzamidine; (12) p-nitrobenzene sulphonamide is reacted with N-diethyloxamic acid chloride to give p-nitrobenzenesulphondiethylamideoxamide which is converted by phosphorus pentachloride into imido chloride which is reduced to N-(p-aminobenzenesulphon)- N<SP>1</SP>-diethylamido-oxamidine; (13) p-nitrobenzenesulphon-chloracetamide is treated with phosphorus pentachloride and then with dimethylamine and reduced to N-(p-aminobenzenesulphon) -N<SP>1</SP> -dimethyl- N" - dimethyl - aminoacetamidine ; (14)p-nitrobenzenesulphonhexahydrobenzamide is treated with phosphorus pentachloride and then with ammonia and reduced to N-(p-aminobenzenesulphon)-hexahydrobenzamidine. (15) p-Nitrobenzenesulphonic acid chloride is reacted with isovalerylamidine hydrochloride to give N-(p-nitrobenzenesulphon)-isovalerylamidine, which is then reduced to the amino compound. Samples have been furnished under Sect. 2 (5) of compounds which have been prepared according to the following schedules :-(1) Furanoyl chloride is reacted with p-nitrobenzenesulphonamide in the presence of aluminium chloride, the amide so obtained reacted with phosphorus pentachloride and then with ammonia and the nitro-amidine reduced to give N-(p-aminobenzenesulphon) furanoylamidine. (2) p- Nitrobenzenesulphonamide is reacted with p-nitrobenzoyl chloride, then with phosphorus pentachloride, and then with isopropylamine. Reduction gives N-(p-aminobenzenesulphon)- N'-isopropyl-p-aminobenzamidine. (3) Isopropylamine is reacted with the imido chloride of p-nitrobenzenesulphon-furanoylamide and reduced to N-(p-aminobenzenesulphon)-N<SP>1</SP>-isopropyl-furanoylamidine. (4) Butylamine is reacted with the imido chloride of p-nitropenzenesulphonfuranoylamide and reduced to N - (p - aminobenzenesulphon) - N<SP>1</SP> - - n - butyl furanoylamidine. (5) Methylamine is reacted with the imidochloride of p-nitrobenzenesulphon-p-nitro-benzamide, and reduced to N - (p - aminobenzenesulphon) - N<SP>1</SP> - methyl - p-aminobenzamidine. (6) p-Nitrobenzenesulphon-p<SP>1</SP>-chloro-phenylacetamide is reacted with phosphorus pentachloride and then with ammonia and finally reduced to N-(p-aminobenzenesulphon) -p<SP>1</SP>- chloro - phenylacetamidine. (7) The imidochloride obtained as in schedule (6) is treated with methylamine and reduced to N - (p - aminobenzenesulphon) - N<SP>1</SP> - methyl - p - chlorophenylacetamidine. (8) The imidochloride obtained as in schedule (6) is treated with ethylamine and reduced to N-(p-aminobenzenesulphon) - N<SP>1</SP> - ethyl - p - chlorophenylacetamidine. (9) p- Nitrobenzenesulphon-cinnamylamide is reacted with phosphorus pentachloride to give an imidochloride which is treated with ammonia and reduced to N-(p-aminobenzenesulphon)-cinnamylamidine. (10) Fencholic acid chloride is reacted with p-nitrobenzenesulphonamide in the presence of aluminium chloride and the p-nitrobenzenesulphon-fencholylamide reacted with phosphorus pentachloride and then reduced to give N-(p-aminobenzenesulphon)-fencholy lamidine. The Specification as open to inspection under Sect. 91 includes also the treatments of benzenesulphon acylamides which are substituted in the p-position by any group containing nitrogen or a, derivative thereof having a p-substitute which can be converted into a group containing nitrogen. Groups specified in addition to a nitro group or an acylamino group include azo. azoxy. and azomethine group. Additional acids which are specified as suitable for the acyl residue of the benzenesulphonacylamide include α- or #-substituted acrylic acids such as crotonic acid, also camphoric acid, a pyrone carboxylic acid, dimethyloxazole carboxylic acids, paramethoxy benzoic acid, veratric acid and toluylic acid. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH538822X | 1939-12-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB538822A true GB538822A (en) | 1941-08-18 |
Family
ID=4518940
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2065/40A Expired GB538822A (en) | 1939-12-19 | 1940-02-02 | Manufacture of amidine derivatives |
Country Status (1)
Country | Link |
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GB (1) | GB538822A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2457371A (en) * | 1943-11-05 | 1948-12-28 | Geigy Ag J R | Acylated p-aminobenzene sulfonamides |
FR2051545A1 (en) * | 1969-05-19 | 1971-04-09 | Pfizer | |
EP0106080A1 (en) * | 1982-10-20 | 1984-04-25 | LUDWIG HEUMANN & CO GMBH | Heterocyclic compounds, process for their preparation and therapeutic agents containing these compounds |
CN112300093A (en) * | 2020-11-18 | 2021-02-02 | 长江师范学院 | Sulfonyl formamidine compound and synthesis method and application thereof |
-
1940
- 1940-02-02 GB GB2065/40A patent/GB538822A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2457371A (en) * | 1943-11-05 | 1948-12-28 | Geigy Ag J R | Acylated p-aminobenzene sulfonamides |
FR2051545A1 (en) * | 1969-05-19 | 1971-04-09 | Pfizer | |
EP0106080A1 (en) * | 1982-10-20 | 1984-04-25 | LUDWIG HEUMANN & CO GMBH | Heterocyclic compounds, process for their preparation and therapeutic agents containing these compounds |
US4596811A (en) * | 1982-10-20 | 1986-06-24 | Ludwig Heumann & Co., Gmbh | Heterocyclic compounds, a process for their production and medicaments containing these compounds |
CN112300093A (en) * | 2020-11-18 | 2021-02-02 | 长江师范学院 | Sulfonyl formamidine compound and synthesis method and application thereof |
CN112300093B (en) * | 2020-11-18 | 2023-02-24 | 长江师范学院 | Sulfonyl formamidine compound and synthesis method and application thereof |
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