1,3-Dichloroacetone → 4-[2-(4-Chloromethyl-2-oxazolyl)ethyl]-5-methyl-2-phenyloxazole

HRID 1294180Notes

Reaction equation

HRID 1294180 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([NH2:17])=[O:16].[Cl:18][CH2:19][C:20](=O)[CH2:21]Cl.C(=O)([O-])[O-].[K+].[K+]>>[Cl:18][CH2:19][C:20]1[N:17]=[C:15]([CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])[O:16][CH:21]=1

Participants

4

Reactant 3

HCID 107931,3-DichloroacetoneHCID 11430Potassium CarbonateHCID 178613843-(5-Methyl-2-phenyl-4-oxazolyl)propanamide

Product 1

HCID 178612164-[2-(4-Chloromethyl-2-oxazolyl)ethyl]-5-methyl-2-phenyloxazoleYield 18%

Conditions

Temperature
130 °C

Procedure

A mixture of 3-(5-methyl-2-phenyl-4-oxazolyl)propanamide (10.0 g) and 1,3-dichloro-2-propanone (5.35 g) was stirred at 130° C. for 2 hrs. An aqueous potassium carbonate solution was added to alkalize the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue was subjected to silica gel column chromatography to give crystals (2.30 g, 18%) of 4-[2-(4-chloromethyl-2-oxazolyl)ethyl]-5-methyl-2-phenyloxazole from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 71-72° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-3ba4c36890a8468588265f4c9e0c02b6
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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