CH370399A - Verfahren zur Herstellung von neuen Sulfamylbenzamiden - Google Patents

Verfahren zur Herstellung von neuen Sulfamylbenzamiden

Info

Publication number: CH370399A
Authority: CH; Switzerland
Prior art keywords: alkyl; formula; parts; sulfamyl; acid
Prior art date: 1958-03-04

Application number

CH5660158A

Other languages

German (de)

English (en)

Inventor

Wilfried Dr Graf

Erich Dr Schmid

G Dr Stoll Willy

Original Assignee

Geigy Ag J R

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.)

1958-03-04

Filing date

1958-03-04

Publication date

1963-07-15

1958-03-04 Application filed by Geigy Ag J R filed Critical Geigy Ag J R

1958-03-04 Priority to CH5660158A priority Critical patent/CH370399A/de

1959-03-03 Priority to ES0247667A priority patent/ES247667A1/es

1959-03-03 Priority to ES0247668A priority patent/ES247668A1/es

1963-07-15 Publication of CH370399A publication Critical patent/CH370399A/de

Links

238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 5
-1 sulfamyl benzamides Chemical class 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
229940054066 benzamide antipsychotics Drugs 0.000 claims 1
150000002440 hydroxy compounds Chemical class 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
SCYSJFKWFQZRJW-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC(C(Cl)=O)=CC=C1Cl SCYSJFKWFQZRJW-UHFFFAOYSA-N 0.000 description 7
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
FHQAWINGVCDTTG-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=CC=C1Cl FHQAWINGVCDTTG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
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 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
150000005340 3-nitrobenzoic acids Chemical class 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
150000001559 benzoic acids Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
239000000155 melt Substances 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
ZSHHRBYVHTVRFK-UHFFFAOYSA-N 2,4-dichloro-5-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=C(Cl)C=C1Cl ZSHHRBYVHTVRFK-UHFFFAOYSA-N 0.000 description 1
KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
BJJDXAFKCKSLTE-UHFFFAOYSA-N 2,6-dimethylpyrimidin-4-amine Chemical compound CC1=CC(N)=NC(C)=N1 BJJDXAFKCKSLTE-UHFFFAOYSA-N 0.000 description 1
IDQNBVFPZMCDDN-UHFFFAOYSA-N 2-Amino-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(N)=N1 IDQNBVFPZMCDDN-UHFFFAOYSA-N 0.000 description 1
GHCFWKFREBNSPC-UHFFFAOYSA-N 2-Amino-4-methylpyrimidine Chemical compound CC1=CC=NC(N)=N1 GHCFWKFREBNSPC-UHFFFAOYSA-N 0.000 description 1
KGGYATOAILBNDO-UHFFFAOYSA-N 2-chloro-5-(morpholine-4-carbonyl)benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)N2CCOCC2)=C1 KGGYATOAILBNDO-UHFFFAOYSA-N 0.000 description 1
PBJSZPBJCGBELF-UHFFFAOYSA-N 2-chloro-5-(piperidine-1-carbonyl)benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)N2CCCCC2)=C1 PBJSZPBJCGBELF-UHFFFAOYSA-N 0.000 description 1
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 1
IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 description 1
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
VXDHQYLFEYUMFY-UHFFFAOYSA-N 2-methylprop-2-en-1-amine Chemical compound CC(=C)CN VXDHQYLFEYUMFY-UHFFFAOYSA-N 0.000 description 1
SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
XPJVOWIAQQEUFK-UHFFFAOYSA-N 3,4-dimethyl-5-sulfamoylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1C XPJVOWIAQQEUFK-UHFFFAOYSA-N 0.000 description 1
SCPFVKVGZDYEMY-UHFFFAOYSA-N 3-chloro-4-methyl-5-sulfamoylbenzoic acid Chemical compound CC1=C(Cl)C=C(C(O)=O)C=C1S(N)(=O)=O SCPFVKVGZDYEMY-UHFFFAOYSA-N 0.000 description 1
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
LMRKXSDOAFUINK-UHFFFAOYSA-N 3-chlorosulfonylbenzoic acid Chemical class OC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 LMRKXSDOAFUINK-UHFFFAOYSA-N 0.000 description 1
KCHLDNLIJVSRPK-UHFFFAOYSA-N 3-methylsulfanylaniline Chemical compound CSC1=CC=CC(N)=C1 KCHLDNLIJVSRPK-UHFFFAOYSA-N 0.000 description 1
NAETXYOXMDYNLE-UHFFFAOYSA-N 3-sulfamoylbenzoic acid Chemical class NS(=O)(=O)C1=CC=CC(C(O)=O)=C1 NAETXYOXMDYNLE-UHFFFAOYSA-N 0.000 description 1
QMWGSOMVXSRXQX-UHFFFAOYSA-N 3-sulfobenzoic acid Chemical class OC(=O)C1=CC=CC(S(O)(=O)=O)=C1 QMWGSOMVXSRXQX-UHFFFAOYSA-N 0.000 description 1
KVHFZZUPCXCRIX-UHFFFAOYSA-N 4,6-dimethoxy-1,3,5-triazin-2-amine Chemical compound COC1=NC(N)=NC(OC)=N1 KVHFZZUPCXCRIX-UHFFFAOYSA-N 0.000 description 1
RKPDBBKAUGTFAI-UHFFFAOYSA-N 4-(2-methylpropyl)-3-sulfamoylbenzoic acid Chemical compound S(N)(=O)(=O)C=1C=C(C(=O)O)C=CC1CC(C)C RKPDBBKAUGTFAI-UHFFFAOYSA-N 0.000 description 1
NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
XDNAVLYDHZTCRB-UHFFFAOYSA-N 4-bromo-3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=CC=C1Br XDNAVLYDHZTCRB-UHFFFAOYSA-N 0.000 description 1
WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
IGWDFVDYQCWSJU-UHFFFAOYSA-N 4-butoxy-3-sulfamoylbenzoic acid Chemical compound CCCCOC1=CC=C(C(O)=O)C=C1S(N)(=O)=O IGWDFVDYQCWSJU-UHFFFAOYSA-N 0.000 description 1
DAQWWRWCFMXRBX-UHFFFAOYSA-N 4-chloro-n-(4-chlorophenyl)-3-sulfamoylbenzamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)NC=2C=CC(Cl)=CC=2)=C1 DAQWWRWCFMXRBX-UHFFFAOYSA-N 0.000 description 1
MJMUETZDHJPQMK-UHFFFAOYSA-N 4-chloro-n-hexyl-3-sulfamoylbenzamide Chemical compound CCCCCCNC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 MJMUETZDHJPQMK-UHFFFAOYSA-N 0.000 description 1
HFDYDVAJJFNUJI-UHFFFAOYSA-N 4-chloro-n-methyl-3-sulfamoylbenzamide Chemical compound CNC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 HFDYDVAJJFNUJI-UHFFFAOYSA-N 0.000 description 1
VHBBIDGPWBNOJU-UHFFFAOYSA-N 4-chloro-n-phenyl-3-sulfamoylbenzamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)NC=2C=CC=CC=2)=C1 VHBBIDGPWBNOJU-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
HGIOLDSNRBMSKR-UHFFFAOYSA-N 4-ethoxy-3-sulfamoylbenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1S(N)(=O)=O HGIOLDSNRBMSKR-UHFFFAOYSA-N 0.000 description 1
IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
MMNUTYDSZYYWIB-UHFFFAOYSA-N 4-ethyl-3-sulfamoylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1S(N)(=O)=O MMNUTYDSZYYWIB-UHFFFAOYSA-N 0.000 description 1
XALBAJJLPMHBMH-UHFFFAOYSA-N 4-hydroxy-3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=CC=C1O XALBAJJLPMHBMH-UHFFFAOYSA-N 0.000 description 1
CKCJWLSXMXMIQO-UHFFFAOYSA-N 4-methoxy-3-sulfamoylbenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1S(N)(=O)=O CKCJWLSXMXMIQO-UHFFFAOYSA-N 0.000 description 1
OUQMXTJYCAJLGO-UHFFFAOYSA-N 4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(N)=N1 OUQMXTJYCAJLGO-UHFFFAOYSA-N 0.000 description 1
USYIWRQZOYSBNN-UHFFFAOYSA-N 4-methyl-3-sulfamoylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1S(N)(=O)=O USYIWRQZOYSBNN-UHFFFAOYSA-N 0.000 description 1
XALXFSQVBICFKL-UHFFFAOYSA-N 4-propan-2-yl-3-sulfamoylbenzoic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C=C1S(N)(=O)=O XALXFSQVBICFKL-UHFFFAOYSA-N 0.000 description 1
KTQBOXVPFATYMO-UHFFFAOYSA-N 4-propan-2-yloxy-3-sulfamoylbenzoic acid Chemical compound CC(C)OC1=CC=C(C(O)=O)C=C1S(N)(=O)=O KTQBOXVPFATYMO-UHFFFAOYSA-N 0.000 description 1
VQMHZIXTBMKNOI-UHFFFAOYSA-N CC1=CC(C(N)=O)=C(C)C(S(N)(=O)=O)=C1Cl Chemical compound CC1=CC(C(N)=O)=C(C)C(S(N)(=O)=O)=C1Cl VQMHZIXTBMKNOI-UHFFFAOYSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
229960004979 fampridine Drugs 0.000 description 1
239000012362 glacial acetic acid Substances 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
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
WYYNCUOWLSTTRQ-UHFFFAOYSA-N n-benzyl-4-chloro-3-sulfamoylbenzamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)NCC=2C=CC=CC=2)=C1 WYYNCUOWLSTTRQ-UHFFFAOYSA-N 0.000 description 1
DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH5660158A 1958-03-04 1958-03-04 Verfahren zur Herstellung von neuen Sulfamylbenzamiden CH370399A (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CH5660158A CH370399A (de)	1958-03-04	1958-03-04	Verfahren zur Herstellung von neuen Sulfamylbenzamiden
ES0247667A ES247667A1 (es)	1958-03-04	1959-03-03	Procedimiento para la preparacion de nuevas sulfamil-benzamidas
ES0247668A ES247668A1 (es)	1958-03-04	1959-03-03	Procedimiento para la preparacion de nuevas sulfamil-benzamidas

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH5660158A CH370399A (de)	1958-03-04	1958-03-04	Verfahren zur Herstellung von neuen Sulfamylbenzamiden

Publications (1)

Publication Number	Publication Date
CH370399A true CH370399A (de)	1963-07-15

Family

ID=4520595

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH5660158A CH370399A (de)	1958-03-04	1958-03-04	Verfahren zur Herstellung von neuen Sulfamylbenzamiden

Country Status (2)

Country	Link
CH (1)	CH370399A (es)
ES (2)	ES247668A1 (es)

1958
- 1958-03-04 CH CH5660158A patent/CH370399A/de unknown
1959
- 1959-03-03 ES ES0247668A patent/ES247668A1/es not_active Expired
- 1959-03-03 ES ES0247667A patent/ES247667A1/es not_active Expired

Also Published As

Publication number	Publication date
ES247667A1 (es)	1959-12-16
ES247668A1 (es)	1959-12-16

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DE2500157A1 (de)	1976-07-22	Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung
CH645625A5 (de)	1984-10-15	Benzoesaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel.
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AT268323B (de)	1969-02-10	Verfahren zur Herstellung von neuen 3,1-Benzothiazin-Derivaten und ihren Salzen
DE962336C (de)	1957-04-18	Verfahren zur Herstellung von basisch substituierten Carbonsaeureamiden
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