Hydrochloric Acid → 3-Nitro-5-sulphamyl-4-(m-trifluoromethylphenoxy)-benzoic acid

HRID 1287717Notes

Reaction equation

HRID 1287717 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].[F:18][C:19]([F:28])([F:27])[C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.Cl>C(=O)(O)[O-].[Na+]>[N+:15]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])[C:2]=1[O:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:18])([F:27])[F:28])[CH:21]=1)[C:6]([OH:8])=[O:7])([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73763-(Trifluoromethyl)phenolHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 213121533-Nitro-5-sulphamyl-4-(m-trifluoromethylphenoxy)-benzoic acid

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 4-chloro-3-nitro-5-sulphamyl-benzoic acid (7 g), m-trifluoromethylphenol (20 g), and 1N sodium bicarbonate (100 ml) was stirred at 95° C for 6 hours. Then the reaction mixture was acidified by the addition of 4N hydrochloric acid and the excess of trifluoromethylphenol was removed by steam distillation. After cooling, the precipitated 3-nitro-5-sulphamyl-4-(m-trifluoromethylphenoxy)-benzoic acid was collected by suction and recrystallized several times from methanol-water. The melting point of the pure compound was 205°-206° C.

Workup

  1. customthe excess of trifluoromethylphenol was removed by steam distillation
  2. temperatureAfter cooling
  3. customthe precipitated 3-nitro-5-sulphamyl-4-(m-trifluoromethylphenoxy)-benzoic acid was collected by suction
  4. customrecrystallized several times from methanol-water
  5. customwas 205°-206° C.

Sources & evidence

ORD record
ord-b9536b1eceea461d8d566f5898cecd27
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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