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

HRID 1294182Notes

Reaction equation

HRID 1294182 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](=[S:17])[NH2:16].[Cl:18][CH2:19][C:20](=O)[CH2:21]Cl>C(O)C>[Cl:18][CH2:19][C:20]1[N:16]=[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])[S:17][CH:21]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 178612323-(5-Methyl-2-phenyl-4-oxazolyl)propanethioamide

Product 1

HCID 178613444-[2-(4-Chloromethyl-2-thiazolyl)ethyl]-5-methyl-2-phenyloxazoleYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(5-methyl-2-phenyl-4-oxazolyl)propanethioamide (5.47 g), 1,3-dichloro-2-propanone (3.10 g) and ethanol (100 mL) was heated under reflux for 1 hr. The reaction mixture was concentrated, and ethyl acetate was added to the residue. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (3.50 g, 49%) of 4-[2-(4-chloromethyl-2-thiazolyl)ethyl]-5-methyl-2-phenyloxazole from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 89-90° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-38c30d2b989d454a968e02cb74e21897
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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