Triethylamine → 2-Chloro-N-[2-methyl-6-(trifluoromethyl)phenyl]acetamide

HRID 2290960Notes

Reaction equation

HRID 2290960 reaction equation
Cl[CH2:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[C:4]=1[NH:5][C:6](=[O:9])[CH2:7][Cl:8].C(N(CC)CC)C>C(O)C.[Pd]>[CH3:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[C:4]=1[NH:5][C:6](=[O:9])[CH2:7][Cl:8]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 133914032-Chloro-N-[2-(chloromethyl)-6-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 133911942-Chloro-N-[2-methyl-6-(trifluoromethyl)phenyl]acetamideYield 105%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8.01 g (0.0262 mol based on 93.5% assay) of 2'-(chloromethyl)-6'-(trifluoromethyl)-2-chloroacetanilide (prepared as in example 6) and 4.0 ml (0.029 mol) of triethylamine in 60 ml of ethanol was shaken with 0.160 g of 10% Pd/C under 20-50 psi of H2 pressure at room temperature. When H2 uptake was complete (4.0 hr.), the mixture was filtered to remove catalyst and partitioned between 100 ml of methylene chloride and 50 ml of water. The organic phase, combined with a small methylene chloride wash of the aqueous phase, was washed with two 50 ml portions of water and was dried using magnesium sulfate. Solvent removal in vacuo provided 6.92 g of white 2'-methyl-6'-(trifluoromethyl)-2-chloroacetanilide assaying 92.1% for a yield of 96.7%.

Workup

  1. custom(4.0 hr.)
  2. filtrationthe mixture was filtered
  3. customto remove catalyst
  4. custompartitioned between 100 ml of methylene chloride and 50 ml of water
  5. washwash of the aqueous phase
  6. washwas washed with two 50 ml portions of water
  7. customwas dried
  8. customSolvent removal in vacuo

Sources & evidence

ORD record
ord-6e975b00352246e08765eafcb6f71b10
Source dataset
uspto-grants-1986_10
Patent number
US04618713

Reaction notes

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