Benzamide → 4-(Chloromethyl)-2-phenyl-1,3-oxazole

HRID 914471Notes

Reaction equation

HRID 914471 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][CH2:11][C:12]([CH2:14]Cl)=O>C(O)C>[Cl:10][CH2:11][C:12]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:8][CH:14]=1

Participants

4

Reactant 2

HCID 2331BenzamideHCID 107931,3-Dichloroacetone

Product 1

HCID 35511964-(Chloromethyl)-2-phenyl-1,3-oxazoleYield 28.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzamide (10.0 g) and 1,3-dichloroacetone (10.5 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=7:1) to give the title compound (4.6 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=7:1)

Sources & evidence

ORD record
ord-a24c3042f84844d89602f097f4801a14
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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