Hydrochloric Acid → 4-Chloro-5-(2-acetamidophenylsulfamoyl)-3-nitrobenzoic acid
Reaction equation
[Cl:1][C:2]1[C:10]([S:11](Cl)(=[O:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].N[CH2:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21].C[N:30](C)C=O.Cl>O>[Cl:1][C:2]1[C:10]([S:11](=[O:13])(=[O:12])[NH:30][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[NH:22][C:20](=[O:21])[CH3:19])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]Participants
6
Procedure
The starting material is prepared as follows: The mixture of 38.8 g 4-chloro-5-chlorosulfonyl-3-nitrobenzoic acid, 39.9 g of 2-aminoacetanilide and 150 ml of dimethylformamide is stirred for 21/2 hours at room temperature. It is poured into 1.7 lt of water and 20 ml of concentrated hydrochloric acid while stirring, the precipitate formed is filtered off and washed with water. It is dissolved in 600 ml of hot ethanol, 900 ml of hot water are added, the mixture filtered and the filtrate left in the cold, to yield the 4-chloro-5-(2-acetamidophenylsulfamoyl)-3-nitrobenzoic acid melting at 225°-227° with decomposition. [In the analogous manner the 5-(4-acetamidophenylsulfamoyl)-isomer is prepared, m.p. 245°-246° (dec.).]
Workup
- customThe starting material is prepared
- stirringwhile stirring
- customthe precipitate formed
- filtrationis filtered off
- washwashed with water
- dissolutionIt is dissolved in 600 ml of hot ethanol
- addition900 ml of hot water are added
- filtrationthe mixture filtered
- waitthe filtrate left in the cold,
Sources & evidence
- ORD record
- ord-0ccf42553e5c4925ab0020e4e6555b4a
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03933906
Reaction notes
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