Hydrochloric Acid → 4-Chloro-5-(2-acetamidophenylsulfamoyl)-3-nitrobenzoic acid

HRID 1578852Notes

Reaction equation

HRID 1578852 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

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 898924-Chloro-5-chlorosulfonyl-3-nitrobenzoic acidHCID 2083842-Aminoacetanilide

Product 1

HCID 215589374-Chloro-5-(2-acetamidophenylsulfamoyl)-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 2 1/2 hours at room temperature. It is poured into 1.7 1t 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.

Workup

  1. customThe starting material is prepared
  2. stirringwhile stirring
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washwashed with water
  6. dissolutionIt is dissolved in 600 ml of hot ethanol
  7. addition900 ml of hot water are added
  8. filtrationthe mixture filtered
  9. waitthe filtrate left in the cold,

Sources & evidence

ORD record
ord-4c61690541e04cdaa53fe8bbb56df48e
Source dataset
uspto-grants-1976_02
Patent number
US03939267

Reaction notes

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