Ammonia → HCID 21520067, compound
Reaction equation
Cl[S:2]([C:5]1[C:6]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]([S:14][CH2:15][CH3:16])[CH:8]=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].[NH3:24]>>[CH2:15]([S:14][C:7]1[CH:8]=[C:9]([CH:13]=[C:5]([S:2](=[O:4])(=[O:3])[NH2:24])[C:6]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]([OH:12])=[O:11])[CH3:16]Participants
3
Procedure
5-Chlorosulfonyl-3-ethylthio-4-phenoxybenzoic acid (1 g) is added to concentrated aqueous ammonia (20 ml) at 5°-10°C. After 30 minutes the reaction mixture is heated on a steam-bath for 1 hour while most of the excess of ammonia was allowed to distill off. After cooling, the precipitated ammonium salt of 3-ethylthio-4-phenoxy-5-sulfamylbenzoic acid is collected by filtration. The salt is dissolved in hot water (75 ml) and the solution acidified by addition of hydrochloric acid. After cooling, the precipitated 3-ethylthio-4-phenoxy-5-sulfamylbenzoic acid is collected by filtration and recrystallized from aqueous ethanol to yield the compound with a melting point of 225°-227°C after drying in vacuo at 80°C.
Workup
- distillationto distill off
- temperatureAfter cooling
- filtrationthe precipitated ammonium salt of 3-ethylthio-4-phenoxy-5-sulfamylbenzoic acid is collected by filtration
- dissolutionThe salt is dissolved in hot water (75 ml)
- additionthe solution acidified by addition of hydrochloric acid
- temperatureAfter cooling
- filtrationthe precipitated 3-ethylthio-4-phenoxy-5-sulfamylbenzoic acid is collected by filtration
- customrecrystallized from aqueous ethanol
- customto yield the compound with a melting point of 225°-227°C
- customafter drying in vacuo at 80°C.
Sources & evidence
- ORD record
- ord-0caae8a156c74ab7873a3707ea7fc3d4
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03972886
Reaction notes
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