Pyridine → 140690-80-8

HRID 1461628Notes

Reaction equation

HRID 1461628 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:13][CH:14]=1.N1C=CC=CC=1.[Cl:25][CH:26]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:27](Cl)=[O:28]>C(OCC)(=O)C>[F:18][C:15]([F:16])([F:17])[C:11]1[CH:10]=[C:9]([NH:8][C:27](=[O:28])[CH:26]([Cl:25])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 73753-(Trifluoromethyl)anilineHCID 102902Chloro(phenyl)acetyl chloride

Product 1

HCID 5079533140690-80-8Yield 89.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A toluene [350 milliliters (mL)] solution of 3-aminobenzotrifluoride [35.5 grams (g) 0.22 mol] and pyridine (19.1 grams, 0.24 mol) was cooled in an ice bath. 2-Chloro-2-phenylacetyl chloride (45.8 grams, 0.24 mol) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (2 ×200 mL) and dried with magnesium sulfate. The solvent was removed in a rotary evaporator to provide the desired N-(3-trifluoromethylphenyl)-2-chloro-2-phenylacetamide (61.6 grams, 89% yield) whose structure was confirmed by nuclear magnetic resonance, infra-red spectroscopy, and mass spectroscopy analysis.

Workup

  1. washwashed with water (2 ×200 mL)
  2. dry with materialdried with magnesium sulfate
  3. customThe solvent was removed in a rotary evaporator

Sources & evidence

ORD record
ord-3779557aae0d4277813e4cf03c5d8e3c
Source dataset
uspto-grants-1991_12
Patent number
US05076832

Reaction notes

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