CH237123A - Process for the preparation of 4-amino-benzenesulfonpropionylamide. - Google Patents
Process for the preparation of 4-amino-benzenesulfonpropionylamide.Info
- Publication number
- CH237123A CH237123A CH237123DA CH237123A CH 237123 A CH237123 A CH 237123A CH 237123D A CH237123D A CH 237123DA CH 237123 A CH237123 A CH 237123A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzenesulfonpropionylamide
- amino
- preparation
- group
- converted
- 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
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000000155 melt Substances 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
- -1 nitro, nitroso, azo, hydrazo Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 238000009835 boiling Methods 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
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 4-Amino-benzolsulfonpropionylamid. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von 4-Amino- benzolsulfonpropionylamid, das dadurch ge kennzeichnet ist, dass man ein Benzolsulfon- propionylamid, das in 4-Stellung zur Sulfon- propionylamidgruppe 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.
<I>Beispiel:</I> 20,2 g 4-Nitro-benzolsulfonamid werden mit 150 cm' Propionsäureanhydrid eineStunde zum Sieden erhitzt und das darauf durch Zusatz von Wasser abgeschiedene 4-Nitro- benzolsulfonpropionylamid aus verdünntem Alkohol umkristallisiert.
In seine Lösung in 57oigem Ammoniak wird dann Schwefelwas serstoff bis zur Sättigung eingeleitet, die Lö- sung zur Trockne eingedampft, der Rück stand in Wasser aufgenommen und das 4 - Amino - benzolsulfonpropionylamid durch Zusatz von Essigsäure gefällt. Smp. <B>130</B> bis 131 .
Die Verbindung ist identisch mit der jenigen des Verfahrens des schweiz. Patentes Nr. 222959 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-benzenesulfonpropionylamide. The present patent relates to a process for the preparation of 4-amino benzenesulfonpropionylamide, which is characterized in that a benzenesulfonpropionylamide which contains a group which can be converted into the amino group by reduction in the 4-position to the sulfonpropionylamide group is used 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.
<I> Example: </I> 20.2 g of 4-nitrobenzenesulfonamide are heated to boiling with 150 cm2 propionic anhydride for one hour and the 4-nitrobenzenesulfonpropionylamide which has then separated out by adding water is recrystallized from dilute alcohol.
Hydrogen sulfide is then passed into its solution in 57% ammonia until it is saturated, the solution is evaporated to dryness, the residue is taken up in water and the 4-amino-benzenesulfonpropionylamide is precipitated by adding acetic acid. M.p. <B> 130 </B> to 131.
The connection is identical to that of the Swiss procedure. Patent No. 222959 and can also be used as a medicinal product and as an intermediate for the manufacture of pharmaceuticals and other technically valuable substances.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE237123X | 1938-02-02 | ||
| CH231060T | 1939-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH237123A true CH237123A (en) | 1945-03-31 |
Family
ID=25727524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH237123D CH237123A (en) | 1938-02-02 | 1939-01-19 | Process for the preparation of 4-amino-benzenesulfonpropionylamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH237123A (en) |
-
1939
- 1939-01-19 CH CH237123D patent/CH237123A/en unknown
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