4-(Trifluoromethyl)aniline → HCID 18953981, compound

HRID 1491663Notes

Reaction equation

HRID 1491663 reaction equation
[CH:1]1([C:4](=[O:11])[CH2:5][C:6]([O:8]CC)=O)[CH2:3][CH2:2]1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH:1]1([C:4](=[O:11])[CH2:5][C:6]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][CH:14]=2)=[O:8])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 262979Ethyl 3-cyclopropyl-3-oxopropanoate

Product 1

HCID 18953981HCID 18953981, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10.14 g (65 mmol) of ethyl 3-cyclopropyl-3-oxopropanoate and 10.47 g (65 mmol) of 4-aminobenzotrifluoride in 100 ml of dry toluene was refluxed for 8 hours using a Dean-Stark condenser to remove the ethanol formed during the reaction. The reaction mixture was cooled and petroleum ether (b.p. 40°-60° C.) was added to obtain 16.44 g (93%) of 3-cyclopropyl-3-oxo-N-[4-(trifluoromethyl)phenyl]-propanamide as a white crystalline solid, melting at 131°-2° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customto remove the ethanol
  3. customformed during the reaction
  4. temperatureThe reaction mixture was cooled

Sources & evidence

ORD record
ord-2835147398b9405ebd23814180c91160
Source dataset
uspto-grants-1994_12
Patent number
US05371099

Reaction notes

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