Water → HCID 9857126, compound

HRID 1610941

Reaction equation

HRID 1610941 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.[Cl:16][CH2:17][C:18]([CH2:20]Cl)=O.O>C1(C)C=CC=CC=1>[Cl:16][CH2:17][C:18]1[N:13]=[C:11](/[CH:10]=[CH:9]/[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][CH:7]=2)[O:12][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 107931,3-DichloroacetoneHCID 57090144-(Trifluoromethyl)cinnamamide

Product 1

HCID 9857126HCID 9857126, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (E)-3-(4-trifluoromethylphenyl)-2-propenamide (17.9 g) and 1,3-dichloroacetone (14.8 g) in toluene (83 ml) was refluxed for 9 hours by use of Dean-Stark apparatus. After cooling, the reaction mixture was combined with water, extracted with ethyl acetate, washed with saturated brine, and dried over magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=6:1 to 5:1) to give the titled compound (15.1 g) as colorless needle crystals.

Workup

  1. temperaturewas refluxed for 9 hours by use of Dean-Stark apparatus
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=6:1 to 5:1)

Sources & evidence

ORD record
ord-f5e6a1b5218143e3a243ec9ba534379d
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Linked notes

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