Ethanol → 5-Chloro-2-(trifluoromethyl)aniline

HRID 2072588Notes

Reaction equation

HRID 2072588 reaction equation
[NH4+]=S.C(O)C.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:16]([F:19])([F:18])[F:17])=[C:11]([N+:13]([O-])=O)[CH:12]=1>O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:16]([F:17])([F:18])[F:19])=[C:11]([CH:12]=1)[NH2:13]

Participants

4

Reactant 2

HCID 702EthanolHCID 1176534-Chloro-2-nitro-1-(trifluoromethyl)benzene

Product 1

HCID 679635-Chloro-2-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Aqueous ammonium sulfide (60 g., 52-60%) is added dropwise to a warm (75° C.), stirred ethanol solution of 5-chloro-2-trifluoromethylnitrobenzene (22.6 g., 0.1 mole) and the resulting mixture is heated for four hours at a heating bath temperature of 97° C. and then allowed to cool to room temperature. The reaction mixture is poured into water, and the organic product is extracted with diethyl ether. After washing and drying the ether solution, the ether is removed by evaporation to give 5-chloro-2-trifluoromethylaniline.

Workup

  1. temperaturethe resulting mixture is heated for four hours at a heating bath temperature of 97° C.
  2. temperatureto cool to room temperature
  3. extractionthe organic product is extracted with diethyl ether
  4. washAfter washing
  5. dry with materialdrying the ether solution
  6. customthe ether is removed by evaporation

Sources & evidence

ORD record
ord-627367a43146401ebde81589ce787a1a
Source dataset
uspto-grants-1990_04
Patent number
US04913728

Reaction notes

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