Toluene → 4-(chloromethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole

HRID 352054Notes

Reaction equation

HRID 352054 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([NH2:11])=[O:10])=[CH:5][CH:4]=1.[Cl:16][CH2:17][C:18]([CH2:20]Cl)=O.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Cl:16][CH2:17][C:18]1[N:11]=[C:9](/[CH:8]=[CH:7]/[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:13][CH:12]=2)[O:10][CH:20]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 107931,3-DichloroacetoneHCID 27790124-(Trifluoromethyl)-cinnamamide

Product 1

HCID 98571264-(chloromethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazoleYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(Trifluoromethyl)cinnamamide (1 g, 4.65 mmol) and 1,3-dichloroacetone (1.1 g, 8.66 mmol) were added to toluene (5 ml) and the mixture was refluxed under heating for 8 hours. Ethyl acetate (20 ml) was added and the mixture was washed with water (20 ml) twice, and then concentrated under reduced pressure. To the residue was added methanol (4 ml) and the mixture was stirred at room temperature. The crystals were filtrated and dried under reduced pressure to give 4-(chloromethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (733 mg, yield 55%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 8 hours
  3. washthe mixture was washed with water (20 ml) twice
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added methanol (4 ml)
  6. filtrationThe crystals were filtrated
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-4f45326c1c5b42299d72d7fee443b9fa
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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