CH240726A - Process for the preparation of a p-amino-benzenesulfonamide. - Google Patents
Process for the preparation of a p-amino-benzenesulfonamide.Info
- Publication number
- CH240726A CH240726A CH240726DA CH240726A CH 240726 A CH240726 A CH 240726A CH 240726D A CH240726D A CH 240726DA CH 240726 A CH240726 A CH 240726A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- preparation
- dimethyl
- benzenesulfonamide
- nitro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title description 2
- -1 4-nitro-benzenesulphonic acid halide Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229940124530 sulfonamide Drugs 0.000 description 3
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 2
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 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
- C07C311/30—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines p-Amino-benzolsulfonamides. Gegenstand vorliegenden Zusatzpatentes ist ein Verfahren zur Herstellung des be kannten 4 - Amino - Benzol - N, - (ss,ss-dimethyl- acroyl)-sulfonamides, welches dadurch ge kennzeichnet ist, dass man ein 4-Nitro-benzol- sulfonsäurehalogenid mit einem Salz des ss,ss-Dimethyl-acrylsäureamids umsetzt und im entstandenen 4 - Nitro -Benzol - N - (ss,ss-di- methylacroyl)
-sulfonamid die Nitrogruppe zur Aminogruppe reduziert. <I>Beispiel:</I> 10 Teile ss,ss-Dimethyl-acrylsäureamid wer den in 200 Teilen absolutem Toluol gelöst, mit 4 Teilen Natriumamid versetzt und durch .'/2stündiges Sieden ins Natriumsalz überge führt.
Nach dem Erkalten lässt man eine Lö sung von 22 Teilen p-Nitro-benzolsulfochlo- rid in<B>100</B> Teilen absolutem Toluol zufliessen und erhitzt 2 Stunden unter Rühren und Rückfluss: Das Toluol wird im Vakuum ab destilliert, der Rückstand in Soda gelöst, die Lösung filtriert und angesäuert.
Man erhält, aus Alkohol umkristallisiert, das 4-Nitro- benzol - N - (ss,ss - dimethyl - acroyl)-sulfonamid vom Schmelzpunkt 155 , und daraus durch Reduktion die entsprechende Aminoverbin- dung.
Process for the preparation of a p-amino-benzenesulfonamide. The present additional patent is a process for the preparation of the known 4 - amino - benzene - N, - (ss, ss-dimethyl-acroyl) -sulfonamides, which is characterized in that a 4-nitro-benzenesulfonic acid halide with a Reacts salt of ss, ss-dimethyl-acrylamide and in the resulting 4 - nitro-benzene - N - (ss, ss-dimethyl acrylate)
-sulfonamide reduces the nitro group to the amino group. <I> Example: </I> 10 parts of ss, ss-dimethyl-acrylic acid amide are dissolved in 200 parts of absolute toluene, mixed with 4 parts of sodium amide and converted into the sodium salt by boiling for 1/2 hour.
After cooling, a solution of 22 parts of p-nitrobenzenesulfochloride in 100 parts of absolute toluene is allowed to flow in and the mixture is heated for 2 hours with stirring and reflux: the toluene is distilled off in vacuo, the residue dissolved in soda, the solution filtered and acidified.
Recrystallized from alcohol, 4-nitrobenzene-N- (ss, ss-dimethyl-acroyl) -sulfonamide with a melting point of 155 is obtained, and the corresponding amino compound is obtained therefrom by reduction.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH240726T | 1943-04-09 | ||
| CH237880T | 1943-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240726A true CH240726A (en) | 1946-01-15 |
Family
ID=25728283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240726D CH240726A (en) | 1943-04-09 | 1943-04-09 | Process for the preparation of a p-amino-benzenesulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH240726A (en) |
-
1943
- 1943-04-09 CH CH240726D patent/CH240726A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH240726A (en) | Process for the preparation of a p-amino-benzenesulfonamide. | |
| CH242291A (en) | Process for the preparation of a p-amino-benzenesulfonamide. | |
| CH245586A (en) | Process for the preparation of a p-amino-benzenesulfonamide. | |
| CH220971A (en) | Process for the preparation of a condensation product. | |
| DE668968C (en) | Process for the preparation of aminoazaphenanthrenes | |
| CH218517A (en) | Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-isopropyl-ketone. | |
| DE861839C (en) | Process for the preparation of threo-1- (4'-nitrophenyl) -2-dichloroacetylamino-1, 3-dichloropropane | |
| CH238089A (en) | Process for the preparation of 4-amino-benzenesulfone-3'-methyl-4'-methylmercapto-benzamide. | |
| CH245587A (en) | Process for the preparation of a p-amino-benzenesulfonamide. | |
| CH240143A (en) | Process for the preparation of a basic aralkyl ether. | |
| CH236172A (en) | Process for the preparation of 4-amino-benzenesulfone-2'-isopropylmercapto-benzamide. | |
| CH222484A (en) | Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-propyl-ketone. | |
| CH481875A (en) | Process for the preparation of a new amine | |
| CH222959A (en) | Process for the preparation of 4-amino-benzenesulfonpropionylamide. | |
| CH314215A (en) | Process for the preparation of a quaternary ammonium salt | |
| CH296241A (en) | Process for the preparation of N-acrylaminoacetic acid. | |
| CH298684A (en) | Process for the preparation of the dipropargyl ether of 4,4'-dioxy-a, B-diethyl-stilbene. | |
| CH175233A (en) | Process for the preparation of 4-amino-3-benzyloxy-diphenylamine. | |
| CH211294A (en) | Process for the production of a condensation product. | |
| CH239147A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH333078A (en) | Process for the production of new anesthetic agents | |
| CH161978A (en) | Process for the preparation of 4-butylaminobenzoic acid-B-dimethylaminoethyl ester. | |
| CH180874A (en) | Process for the preparation of an acylated dihydrofollicle hormone. | |
| CH255615A (en) | Process for the preparation of an aromatic acylsulfonamide. | |
| CH205789A (en) | Process for the preparation of 6-methyl-2-amino-3-methoxy-diphenylene oxide. |