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

HRID 2290961
Notes
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Reaction equation

HRID 2290961 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(OCC)(=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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.02 g (7.06 mmol) of 2'-(chloromethyl)-6'-(trifluoromethyl)-2-chloroacetanilide and 1.0 ml (7.2 mmol) of triethylamine in 60 ml of ethyl acetate was shaken with 79.8 mg of 10% Pd/C under an initial H2 pressure of 50 psi. After 19 hr., the mixture was filtered and evaporated to give 1.57 g of 2'-methyl-6'-(trifluoromethyl)-2-chloroacetanilide assaying 94.2% (yield 83.3%) and contaminated with 1.3% of overreduced product.

Workup

  1. filtration, the mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-6753d098a53b497ea479dc9214aa9ec5
Source dataset
uspto-grants-1986_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04618713

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes