1,3-Dichloroacetone → 4-(Chloromethyl)-2-(4-methylphenyl)-1,3-oxazole

HRID 914472Notes

Reaction equation

HRID 914472 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][CH2:12][C:13]([CH2:15]Cl)=O>C(O)C>[Cl:11][CH2:12][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=2)[O:7][CH:15]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 692744-Methylbenzamide

Product 1

HCID 155551134-(Chloromethyl)-2-(4-methylphenyl)-1,3-oxazoleYield 50.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methylbenzamide (10.0 g) and 1,3-dichloroacetone (9.4 g) were dissolved in ethanol (100 mL), and the mixture was refluxed for 8 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 7:1) to give the title compound (7.8 g) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 8 hr
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 7:1)

Sources & evidence

ORD record
ord-960be579ba4742aca3d7c8bf68138d91
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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