Water → HCID 9857126, compound

HRID 2084358

Reaction equation

HRID 2084358 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 solution of (E)-3-(4-trifluoromethylphenyl)-2-propenamide (17.9 g) and 1,3-dichloroacetone (14.8 g) in toluene (83 ml) was refluxed under heating for 9 hours using a Dean-Stark apparatus. After cooling, water was added; the reaction mixture was extracted with ethyl acetate and washed with saturated saline, after which it was dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (eluent: hexane-methyl acetate=6:1→5:1) to yield the titled compound (15.1 g) as a colorless needle crystal.

Workup

  1. temperatureunder heating for 9 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washwashed with saturated saline
  5. dry with materialafter which it was dried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: hexane-methyl acetate=6:1→5:1)

Sources & evidence

ORD record
ord-798c87eca15c434aab6813a671a6242d
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Linked notes

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