CH237125A - Process for the preparation of 4-amino-benzenesulfonisovalerylamide. - Google Patents
Process for the preparation of 4-amino-benzenesulfonisovalerylamide.Info
- Publication number
- CH237125A CH237125A CH237125DA CH237125A CH 237125 A CH237125 A CH 237125A CH 237125D A CH237125D A CH 237125DA CH 237125 A CH237125 A CH 237125A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- preparation
- benzenesulfonisovalerylamide
- group
- needles
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 238000005245 sintering Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000003368 amide group Chemical group 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- -1 nitro, nitroso, azo, hydrazo Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
- QWKKYJLAUWFPDB-UHFFFAOYSA-N 4-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 QWKKYJLAUWFPDB-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
Verfahren zur Herstellung von 4-Amino-benzolsulfonisovalerylamid. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von 4-Amino- benzolsulfonisovalerylamid, das dadurch ge kennzeichnet ist, dass man ein Benzolsulfon- isovalerylamid, das in 4-Stellung zur Sulfon- isovalerylamidgruppe eine durch Reduktion in die Aminogruppe überführbare Gruppe enthält, mit einem reduzierenden Mittel be handelt.
Solche in die Aminogruppe überführbare Gruppen sind die Nitro-, Nitroso-, Azo-, Hydrazo-, Azogy-, Benzylamino-, Carbo- benzylogyamino- und dergleichen Gruppen.
Beispiel: 20,2 g 4-Nitro-benzolsulfonamid werden in 250 cm:3 Pyridin gelöst und unter Rühren bei gewöhnlicher Temperatur langsam mit 2'4,2 g Isovalerylchlorid versetzt. Zur Be endigung der Reaktion wird noch eine Stunde auf 80 bis 90 erwärmt, dann die erkaltete Lösung in Wasser gegossen, mit Salzsäure angesäuert und der Niederschlag umkristallisiert.
Das erhaltene Nitroprodukt wird dann in 5%igem Ammoniak gelöst, in die Lösung Schwefelwasserstoff bis zur Sättigung eingeleitet, dann zur Trockne ein gedampft, der Rückstand mit Wasser auf genommen und das 4-Amino-benzolsulfon- isovalerylamid durch Zusatz von Essigsäure als ölige, aber bald fest werdende Masse er halten. Nach. Umfällung schmilzt die Ver bindung unter Sinterung bei 100 . Beim vor sichtigen Umlösen aus verdünntem Alkohol werden Nadeln vom Schmelzpunkt 123 er halten.
Die Verbindung ist identisch mit der jenigen des Verfahrens des schweiz. Patentes Nr. 222967 und kann ebenfalls als Arznei mittel, sowie als Zwischenprodukt zur Her stellung von Arzneimitteln und andern tech nisch wertvollen Substanzen Verwendung finden.
Process for the preparation of 4-amino-benzenesulfonisovalerylamide. The present patent relates to a process for the preparation of 4-Amino-benzenesulfonisovalerylamide, which is characterized in that a benzenesulfonisovalerylamide, which in the 4-position to the sulfonisovalerylamidgruppe contains a group which can be converted into the amino group by reduction, with a reducing agents.
Such groups which can be converted into the amino group are the nitro, nitroso, azo, hydrazo, azogy, benzylamino, carbobenzylogyamino and the like groups.
Example: 20.2 g of 4-nitrobenzenesulfonamide are dissolved in 250 cm: 3 pyridine and, while stirring, slowly mixed with 2.4.2 g of isovaleryl chloride at normal temperature. To end the reaction, the mixture is heated to 80 to 90 for another hour, then the cooled solution is poured into water, acidified with hydrochloric acid and the precipitate is recrystallized.
The nitro product obtained is then dissolved in 5% ammonia, hydrogen sulfide introduced into the solution until saturation, then evaporated to dryness, the residue taken up with water and the 4-amino-benzenesulfon-isovalerylamide by adding acetic acid as oily, but soon solidifying mass he holds. To. Reprecipitation melts the compound with sintering at 100. When carefully dissolving from dilute alcohol, needles with a melting point of 123 will be obtained.
The connection is identical to that of the Swiss procedure. Patent No. 222967 and can also be used as a medicinal product and as an intermediate for the manufacture of drugs and other technically valuable substances.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE237125X | 1938-02-02 | ||
| CH231060T | 1939-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH237125A true CH237125A (en) | 1945-03-31 |
Family
ID=25727526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH237125D CH237125A (en) | 1938-02-02 | 1939-01-19 | Process for the preparation of 4-amino-benzenesulfonisovalerylamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH237125A (en) |
-
1939
- 1939-01-19 CH CH237125D patent/CH237125A/en unknown
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