Acetic Acid → HCID 11550816, compound

HRID 1268883Notes

Reaction equation

HRID 1268883 reaction equation
O=[C:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:10][C:11]([F:20])([F:19])[C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15].C(O)(=O)C>C1(C)C=CC=CC=1>[F:10][C:11]([F:19])([F:20])[C:12]1[CH:13]=[C:14]([NH:15]/[C:2](/[CH3:9])=[CH:3]/[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 73753-(Trifluoromethyl)anilineHCID 8868Ethyl Acetoacetate

Product 1

HCID 11550816HCID 11550816, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.0 g (31 mmol) Ethyl 3-oxobutanoate, 5.0 g (31 mmol) 3-trifluoromethylaniline, and 1.86 g (31 mmol) acetic acid are dissolved in 50 ml toluene. The reaction mixture is refluxed overnight with a Dean-Stark trap to remove water. After cooling down to room temperature, the solvent is removed in vacuo and the residue is purified by column chromatography on silica with cyclohexane/ethylacetate mixtures as eluent.

Workup

  1. temperatureThe reaction mixture is refluxed overnight with a Dean-Stark trap
  2. customto remove water
  3. customthe solvent is removed in vacuo
  4. customthe residue is purified by column chromatography on silica with cyclohexane/ethylacetate

Sources & evidence

ORD record
ord-885b4d96cdbd419794c50499868806b8
Source dataset
uspto-grants-2007_04
Patent number
US07199136B2

Reaction notes

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