3-(Trifluoromethyl)aniline → Acetamide, N-(3-(trifluoromethyl)phenyl)-

HRID 1658736Notes

Reaction equation

HRID 1658736 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[C:12](OC(=O)C)(=[O:14])[CH3:13]>Cl>[CH3:13][C:12]([NH:6][C:5]1[CH:4]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:9]=[CH:8][CH:7]=1)=[O:14]

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 7918Acetic Anhydride

Product 1

HCID 9595Acetamide, N-(3-(trifluoromethyl)phenyl)-Yield 93.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 161.0 g of α, α, α-trifluoro-m-toluidine in 500 ml of 2N hydrochloric acid, at room temperature, with vigorous agitation, is added rapidly 102.0 g of acetic anhydride. An exothermic reaction occurs and the temperature is allowed to rise spontaneously to about 50°. Subsequently, the mixture is allowed to cool to room temperature, and then cooled in ice. The crystalline solid is filtered to give 189.3 g of α,α,α-trifluoro-m-acetotoluidide.

Workup

  1. customAn exothermic reaction
  2. customto rise spontaneously to about 50°
  3. temperaturecooled in ice
  4. filtrationThe crystalline solid is filtered

Sources & evidence

ORD record
ord-d1a3b96bfc1641b9a768d506617af528
Source dataset
uspto-grants-1976_06
Patent number
US03966733

Reaction notes

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