m-Toluidine → 3-Nitro-5-sulphamyl-4-(m-toluidino)-benzoic acid

HRID 1287724Notes

Reaction equation

HRID 1287724 reaction equation
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[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]=[C:21]([CH3:25])[CH:20]=1>O>[N+:15]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])[C:2]=1[NH:18][C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=1)[C:6]([OH:8])=[O:7])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 215059883-Nitro-5-sulphamyl-4-(m-toluidino)-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-3-nitro-5-sulphamyl-benzoic acid (28 g), m-toluidine (32.2 g), and water (500 ml) was refluxed for 3 hours. After cooling and acidification with 2N hydrochloric acid, the precipitated 3-nitro-5-sulphamyl-4-(m-toluidino)-benzoic acid was collected by suction, washed with water, and recrystallized from isopropanol. After drying at 115° C in vacuo, the melting point was 256°-259° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. customacidification with 2N hydrochloric acid, the precipitated 3-nitro-5-sulphamyl-4-(m-toluidino)-benzoic acid was collected by suction
  4. washwashed with water
  5. customrecrystallized from isopropanol
  6. customAfter drying at 115° C in vacuo

Sources & evidence

ORD record
ord-8129aa93cbf54796ac685ecaefc3577b
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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