CH238089A - Process for the preparation of 4-amino-benzenesulfone-3'-methyl-4'-methylmercapto-benzamide. - Google Patents
Process for the preparation of 4-amino-benzenesulfone-3'-methyl-4'-methylmercapto-benzamide.Info
- Publication number
- CH238089A CH238089A CH238089DA CH238089A CH 238089 A CH238089 A CH 238089A CH 238089D A CH238089D A CH 238089DA CH 238089 A CH238089 A CH 238089A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- methyl
- parts
- amino
- benzamide
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- 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
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 4-Amino-benzolsulfon-3'-methyl-4'- methylmer capto-benzamid. Gegenstand des vorliegenden Zusatzpa tentes ist ein Verfahren zur Herstellung von 4-Amino-benzolsulfon-3'-methyl-4'-methylmer- eapto-benzamid, welches dadurch gekennzeich net ist, dass man ein 3-Methyl-4-methylmer- capto-benzoylhalogenid auf p-Acetylamino-ben- zolsulfonamid einwirken lässt und anschliessend die Acetylaminogruppe verseift.
Die neue Verbindung stellt farblose Kristalle vom Schmelzpunkt 192 dar und soll thera peutische Verwendung finden.
<I>Beispiel:</I> 21 Teile p-Acetylamino-benzolsulfonamid werden in 50 Teilen trockenem Pyridin bei 80 gelöst und unter gutem Rühren mit 20 Teilen 3-Methyl-4-methylmercapto-benzoesäurechlorid versetzt. Nach beendeter Reaktion wird mit verdünnter Salzsäure versetzt und das aus geschiedene Produkt abgesaugt.
Es wird nun mit überschüssiger Natron lauge eine Stunde gekocht, wobei die Acetyl- gruppe abgespalten wird. Aus dem Filtrat wird das 4=Amino-benzol- sulfon-3'- methyl-4'- methylmeriapto -benzamid mit verdünnter Essigsäure ausgefällt, abge saugt und aus Alkohol unter Zusatz von Tierkohle umkristallisiert. F. 192 .
Die 3-Methyl-4-methylmercapto-benzoe- säure und ihr Säurechlorid können folgender massen dargestellt werden 22 Teile der 3-3Zethyl-4-aminobenzoesäure (A. 144, 168 werden in einem Gemisch von 200 Teilen Wasser und 30 Teilen konzen trierter Salzsäure heiss gelöst, die Lösung auf 5-10 abgekühlt und dianotiert.
Die Diazonium- lösung wird unter starkem Rühren in eine 70 heisse Lösung von 25 Teilen Kalium- xanthogenat und 20 Teilen Soda in 100 Teilen Wasser einlaufen gelassen.
Nach '/4 Stunde wird auf 30 abgekühlt, die Lösung mit 6,5 Teilen festem Natriumhydroxyd versetzt und, wenn dies gelöst ist, 20 Teile Dimethyl- sulfat zugetropft. Nach einer Stunde wird einige Zeit unter Rückfluss gekocht, dann mit Dampf destilliert und hierauf der Rückstand mit Salzsäure angesäuert.
Die ausgeschiedene Methylthiocarbonsäure wird abgenutscht, ge- trocknet und im Hochvakuum destilliert, gpo,7 180-190 , F. 166-167 .
17 Teile 3-Methyl-4-methylmerca.pto-ben- zoesäure werden mit 30 Vol.-Teilen Thiony 1- chlorid zwei Stunden unter Rückflur erwärmt. Das überschüssige Thionylchlorid wird im Vakuum abgesaugt und das Säurechlorid im Hochvakuum fraktioniert, gpo,s 135-140 , F. 64-65 .
Process for the preparation of 4-amino-benzenesulfon-3'-methyl-4'-methylmer capto-benzamide. The subject of the present additional patent is a process for the production of 4-amino-benzenesulfone-3'-methyl-4'-methylmer- eapto-benzamide, which is characterized in that a 3-methyl-4-methylmer- capto- lets benzoyl halide act on p-acetylamino-benzenesulfonamide and then saponifies the acetylamino group.
The new compound is colorless crystals with a melting point of 192 and is intended to be used therapeutically.
<I> Example: </I> 21 parts of p-acetylamino-benzenesulfonamide are dissolved in 50 parts of dry pyridine at 80, and 20 parts of 3-methyl-4-methylmercaptobenzoic acid chloride are added with thorough stirring. When the reaction has ended, dilute hydrochloric acid is added and the product which has separated out is filtered off with suction.
It is now boiled with excess sodium hydroxide solution for one hour, the acetyl group being split off. The 4 = amino-benzene-sulfone-3'-methyl-4'-methylmeriapto-benzamide is precipitated from the filtrate with dilute acetic acid, filtered off with suction and recrystallized from alcohol with the addition of animal charcoal. F. 192.
The 3-methyl-4-methylmercaptobenzoic acid and its acid chloride can be prepared as follows: 22 parts of 3-3Zethyl-4-aminobenzoic acid (A. 144, 168 are concentrated in a mixture of 200 parts of water and 30 parts of concentrated hydrochloric acid Dissolved hot, the solution cooled to 5-10 and dianotized.
The diazonium solution is allowed to run into a hot solution of 25 parts of potassium xanthate and 20 parts of soda in 100 parts of water with vigorous stirring.
After 1/4 hour the mixture is cooled to 30, the solution is mixed with 6.5 parts of solid sodium hydroxide and, when this has dissolved, 20 parts of dimethyl sulfate are added dropwise. After one hour, the mixture is refluxed for some time, then distilled with steam and the residue is then acidified with hydrochloric acid.
The precipitated methylthiocarboxylic acid is filtered off with suction, dried and distilled in a high vacuum, gpo, 7 180-190, mp 166-167.
17 parts of 3-methyl-4-methylmerca.pto-benzoic acid are refluxed with 30 parts by volume of thionyl 1-chloride for two hours. The excess thionyl chloride is suctioned off in vacuo and the acid chloride fractionated in a high vacuum, gpo, s 135-140, F. 64-65.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH238089T | 1941-10-24 | ||
| CH222076T | 1943-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH238089A true CH238089A (en) | 1945-06-15 |
Family
ID=25726591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH238089D CH238089A (en) | 1941-10-24 | 1941-10-24 | Process for the preparation of 4-amino-benzenesulfone-3'-methyl-4'-methylmercapto-benzamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH238089A (en) |
-
1941
- 1941-10-24 CH CH238089D patent/CH238089A/en unknown
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