2-(Trifluoromethyl)aniline → HCID 178471912, compound

HRID 2104499Notes

Reaction equation

HRID 2104499 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[CH2:12]([O:14][C:15](=[O:29])[C:16]([C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:17]OCC)[CH3:13]>C1(C)C=CC=CC=1>[CH2:12]([O:14][C:15](=[O:29])[C:16]([C:21](=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[CH:17][NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=1[C:2]([F:10])([F:11])[F:1])[CH3:13]

Participants

4

Reactant 2

HCID 69222-(Trifluoromethyl)anilineHCID 98006Ethyl 2-benzoyl-3-ethoxyacrylate

Product 1

HCID 178471912HCID 178471912, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(trifluoromethyl)aniline(4.6 g, 28.8 mmol) and 2-benzoyl-3-ethoxy-acrylic acid ethyl ester 7.2 g, 28.8 mmol) in toluene (125 ml) was heated to reflux. After 18 hr, the reaction was cooled, concentrated and purified by column chromatography (eluent 10% EtOAc/hexane) to give 2-benzoyl-3-(2-trifluoromethyl-phenylamino)-acrylic acid ethyl ester (8.6 g, Yield=82%); MS (ESI) m/z 364(M+H)+; Anal Calcd for C19H16F3NO3: C, 62.81; H, 4.44; N, 3.85. Found: C, 62.87; H, 4.21; N, 3.76.

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe reaction was cooled
  3. concentrationconcentrated
  4. custompurified by column chromatography (eluent 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-a71064ec86f544f98027c2418cd6c3cf
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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