CH229083A - Process for the preparation of a new benzenesulfonamide derivative. - Google Patents
Process for the preparation of a new benzenesulfonamide derivative.Info
- Publication number
- CH229083A CH229083A CH229083DA CH229083A CH 229083 A CH229083 A CH 229083A CH 229083D A CH229083D A CH 229083DA CH 229083 A CH229083 A CH 229083A
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- reaction
- preparation
- new
- agents
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000008331 benzenesulfonamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- -1 diogan Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines neuen Benzolsulfonamidderivates. Gegensitand des vorliegenden Patentes bil det ein Vorfahren zur Darstellung eines neuen Benzolsulif onamidderivates, welches da,- durch gekennzeichnet ist,,
dass man eine Ver bindung der Formel
EMI0001.0013
worin R eine Acylgruppe und X einen bei .der Reaktion sich abspaltenden Rest bedeu ten, wie z.
B. ein Acylsulfanilsäurehalogenid, auf eine Verbindung -der Formel
EMI0001.0021
worin Y einen bei der Reaktion sich ajbspal- tenden Rest darstellt, einwirken lässt und,die erhaltene Verbindung mit hydrolysierenden Mitteln behandelt.
Das so erhaltene 2-(p- Aminobenzoleulfonamlo) - thio,diazol - (1,3,4) . zeigt den F.218-219 . Es ist in Alkalien sowie in Säuren löslich und gibt die Diazo- i reaktion.
Die neue Verbindung ,soll therapeutische Verwendung finden, Die Kondensation kann in An- oder Ab wesenheit von. indifferenten Lösungsmitteln oder im. Gegenwart von Wasser ausgeführt werden. Als Lösungsmittel lassen sieh z. B.
Äther, Diogan, Petroläther, Benzol, Toluol, Xylol, Chlorbenzol, Nitrobenzol, Tetraahlor- äthan verwenden. Es kann auch in Gegen- wart von Kondensationsmitteln oder Kataly- satoren .gearbeitet werden.
So kann die Um setzung zum Beispiel mit alkalisch .reagie- renden Mitteln., wie Alkalien, und Erdalka lien, organischen Basen, z. B. tertiären Basen wie Pyridin, und @dergleiehen erfolgen.
Zur Hydrolyse können alkalische oder saure Mittel, beispielsweise Alkali- oder Erd- alkalihydrogyde, wie Natrium- oder Calcium- hydrogydoder Säuren, z.
B. Salzsäure in. Gegenwart von Wasser oder organischen Lö- sungsmitte-ln, wie Alkohol, verwendet werden.
Das gebildete 2-,(p,-Aminobenzolsul@fon- ami@do)-thadiazol=(1,3,4) lässt sich als solches oder auch in Form seiner Sallze, z. B.,des Na triums, Calciums oder der Salzsäure, isolieren.
Beispiel: 10 Teile 2-Aminothiodiazal-(1,3,4) wer den in 25 Teilen Pyridin aufgenommen und unter Rühmen allmählich mit 23,5 Teilen p - Acetylaminobenzol'sulfochlorid versetzt.
lIierauf wird noch eine haolbe Stunde auf 95 erhitzt. Durch Eingiessen adererhaltenen Lö sung in, Eiswasser wird das Kondünsations- produkt in fester Form erhalten.
Es wird abgesogen und @durah Kochen in verdünnter Natronlauge verseift. Das mit Essigsäure ausgefällte 2i-(p-Aminobenzalsulfonamid@a)- thio,diiazol-(1,3,4) ha:t naeh dem Umkristalli- sieren aus wässerigem Alkohol den F.218 bis 219 .
Process for the preparation of a new benzenesulfonamide derivative. Subject of the present patent forms an ancestor for the preparation of a new Benzolsulif onamidderivates, which there - is characterized by ,,
that one compound of the formula
EMI0001.0013
where R is an acyl group and X is a residue which is split off during the reaction, such as.
B. an acylsulfanilic acid halide, to a compound of the formula
EMI0001.0021
in which Y represents a radical which splits off during the reaction, allows it to act and treats the compound obtained with hydrolyzing agents.
The 2- (p-aminobenzenesulfonamlo) - thio, diazole - (1,3,4) thus obtained. shows the F.218-219. It is soluble in alkalis as well as acids and gives the diazo reaction.
The new compound is intended to be used therapeutically. The condensation can occur in the presence or absence of. indifferent solvents or im. Presence of water. As a solvent let see z. B.
Use ether, diogan, petroleum ether, benzene, toluene, xylene, chlorobenzene, nitrobenzene, tetraahlorethane. It is also possible to work in the presence of condensation agents or catalysts.
The implementation can, for example, with alkaline .reagie- rende agents., Such as alkalis, and alkaline earths, organic bases, z. B. tertiary bases such as pyridine, and @dergleiehen.
For the hydrolysis, alkaline or acidic agents, for example alkali or alkaline earth metal hydroxides, such as sodium or calcium hydroxide or acids, e.g.
B. hydrochloric acid in the presence of water or organic solvents such as alcohol can be used.
The 2 -, (p, -aminobenzolsul @ fon- ami @ do) -thadiazole = (1,3,4) can be used as such or in the form of its salts, e.g. B., of Na trium, calcium or hydrochloric acid, isolate.
Example: 10 parts of 2-aminothiodiazal (1,3,4) who added to 25 parts of pyridine and gradually admixed with 23.5 parts of p - acetylaminobenzene sulfochloride with stirring.
It is then heated to 95 for half an hour. The condensation product is obtained in solid form by pouring the resulting solution into ice water.
It is sucked off and @durah boiling is saponified in dilute sodium hydroxide solution. The 2i- (p-aminobenzalsulfonamide @ a) -thio, diiazole- (1,3,4) precipitated with acetic acid ha: t after recrystallization from aqueous alcohol, F.218 to 219.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH229083T | 1938-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH229083A true CH229083A (en) | 1943-09-30 |
Family
ID=4455906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH229083D CH229083A (en) | 1938-09-16 | 1938-09-16 | Process for the preparation of a new benzenesulfonamide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH229083A (en) |
-
1938
- 1938-09-16 CH CH229083D patent/CH229083A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH230860A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH230861A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH230863A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH210781A (en) | Process for the preparation of a new benzene sulfamide derivative. | |
| AT163820B (en) | Process for the preparation of a new condensation product of sulfanilamidoethylthiodiazole | |
| CH230865A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH232273A (en) | Process for the production of a cyclopentano-dimethyl-polyhydro-phenanthrene-carboxylic acid. | |
| CH226817A (en) | Process for producing a water-soluble compound. | |
| CH230857A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| DE500162C (en) | Process for the preparation of 4-methyl-6-halogen-3-oxy-1-thionaphthenes | |
| DE540534C (en) | Process for the preparation of alkoxy derivatives of 2-oxynaphthalene-3-carboxylic acid | |
| CH179977A (en) | Process for the preparation of 5-methyl-5-piperidino-barbituric acid. | |
| CH229081A (en) | Process for the preparation of a benzenesulfonamide derivative. | |
| CH239147A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH239153A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH239148A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH242496A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| CH257637A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH100407A (en) | Process for the preparation of diethylaminoethylcarbamic acid phenylethyl ester. | |
| CH210775A (en) | Process for the preparation of a new benzene sulfamide derivative. | |
| AT227256B (en) | Process for the production of new aminoindanes and their salts | |
| CH140622A (en) | Process for the preparation of the 4.4'-arseno-3.3'-dioxy-2.2'-diamino-benzaldehyde thiosemicarbazone. | |
| CH239149A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH105106A (en) | Process for the preparation of an alkoxyakridine. | |
| CH239158A (en) | Process for the production of a new benzene sulfonamide derivative. |