Aniline → 4-Anilino-3-nitro-5-phenylsulphamyl-benzoic acid

HRID 918604Notes

Reaction equation

HRID 918604 reaction equation
Cl[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].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCC)(=O)C>[NH:18]([C:2]1[C:10]([S:11](=[O:13])(=[O:12])[NH:15][C:3]2[CH:4]=[CH:5][CH:9]=[CH:10][CH:2]=2)=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 898924-Chloro-5-chlorosulfonyl-3-nitrobenzoic acid

Product 1

HCID 215060884-Anilino-3-nitro-5-phenylsulphamyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-3-nitro-5-chlorosulphonyl-benzoic acid (6 g) in ethyl acetate (50 ml), aniline (7.5 g) was added, while stirring. The reaction mixture was stirred for a further 8 hours and filtered. The filtrate was evaporated, and the residue was dissolved in a mixture of aqueous sodium hydrogen carbonate and diethyl ether. The aqueous layer was separated, and the 4-anilino-3-nitro-5-phenylsulphamyl-benzoic acid was precipitated by addition of 4N hydrochloric acid. After recrystallization from aqueous ethanol (25% ethanol in water), the melting point was 249°-250°C.

Workup

  1. stirringThe reaction mixture was stirred for a further 8 hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. dissolutionthe residue was dissolved in a mixture of aqueous sodium hydrogen carbonate and diethyl ether
  5. customThe aqueous layer was separated
  6. customthe 4-anilino-3-nitro-5-phenylsulphamyl-benzoic acid was precipitated by addition of 4N hydrochloric acid
  7. customAfter recrystallization from aqueous ethanol (25% ethanol in water)

Sources & evidence

ORD record
ord-7f0fb79a6d864651988750e622130632
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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