1,3-Dichloroacetone → 4-(Chloromethyl)-2-phenyl-1,3-thiazole

HRID 914474Notes

Reaction equation

HRID 914474 reaction equation
[C:1]([NH2:9])(=[S: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>CC(C)=O>[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)[S:8][CH:14]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 683563Thiobenzamide

Product 1

HCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleYield 33.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Thiobenzamide (10.0 g) and 1,3-dichloroacetone (9.25 g) were dissolved in acetone (200 mL), and the mixture was stirred at room temperature for 8 hr. The reaction mixture was concentrated under reduced pressure, methanol (200 mL) was added, and the mixture was refluxed for 1.5 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 (5.1 g) as a brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, methanol (200 mL)
  2. additionwas added
  3. temperaturethe mixture was refluxed for 1.5 hr
  4. temperatureAfter cooling
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-1bb42f8efd1b4f53a058df70d3c6b53a
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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