Ethyl Acetoacetate → HCID 18953978, compound

HRID 1491662Notes

Reaction equation

HRID 1491662 reaction equation
[F:1][C:2]([F:12])([F:11])[S:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[C:13](OCC)(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16]>C1(C)C=CC=CC=1>[F:12][C:2]([F:11])([F:1])[S:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:13](=[O:18])[CH2:14][C:15](=[O:16])[CH3:17])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 1230544-((Trifluoromethyl)thio)aniline

Product 1

HCID 18953978HCID 18953978, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7.72 g (40 mmol of 4-(trifluoromethylthio)aniline and 5.2 g (40 mmol) of ethyl acetoacetate in 80 ml of dry toluene was refluxed for 8 hours using a Dean-Stark trap to remove the ethanol formed during the reaction. The reaction mixture was cooled in an ice-bath to obtain 10.48 g (95%) of N-[4-(trifluoromethylthio)phenyl]-3-oxobutanamide as a white crystalline solid, melting at 120°-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 in an ice-bath

Sources & evidence

ORD record
ord-7219cc9ed80e4b5db802489f2c522c91
Source dataset
uspto-grants-1994_12
Patent number
US05371099

Reaction notes

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