3-(Trifluoromethyl)aniline → N-[3-(Trifluoromethyl)phenyl]-2-chloromethyl-2-methyl-propionamide

HRID 481384Notes

Reaction equation

HRID 481384 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(N(CC)CC)C.[Cl:19][CH2:20][C:21]([CH3:26])([CH3:25])[C:22](Cl)=[O:23]>C(Cl)Cl>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([NH:6][C:22](=[O:23])[C:21]([CH2:20][Cl:19])([CH3:26])[CH3:25])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 613453-Chloro-2,2-dimethylpropanoyl chloride

Product 1

HCID 19066381N-[3-(Trifluoromethyl)phenyl]-2-chloromethyl-2-methyl-propionamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Added to a solution of 16.1 g of 3-(trifluoromethyl)-aniline in methylene chloride were 16.7 ml of triethylamine, and 14.2 ml of 3-chloro-2,2-dimethylpropanoyl chloride were added dropwise under chilling with ice water. After stirring the mixture at room temperature for 1 hour, the resulting liquid reaction mixture was washed once each with water and saturated saline and dried on magnesium sulfate. Methylene chloride was distilled off, and the residue was purified by column chromatography on silica gel to obtain 28 g (yield: 100%) of the title compound.

Workup

  1. additionwere added dropwise
  2. customthe resulting liquid reaction mixture
  3. washwas washed once each with water and saturated saline
  4. customdried on magnesium sulfate
  5. distillationMethylene chloride was distilled off
  6. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-90df33011e9c4d34acd7d2371366c43d
Source dataset
uspto-grants-1998_08
Patent number
US05789419

Reaction notes

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