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

HRID 892147Notes

Reaction equation

HRID 892147 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.C([O-])([O-])=O.[K+].[K+]>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)[S:8][CH:14]=1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 11430Potassium CarbonateHCID 683563Thiobenzamide

Product 1

HCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of thiobenzamide (1.37 g, 10 mmol) and 1,3-dichloro-acetone (1.27 g, 10 mmol) in ethanol (25 mL) is warmed to 75° C. and stirred at this temperature for 1 h. The resulting solution is cooled, poured into ice then brought to pH 8 with K2CO3 solution (sat.). This mixture is extracted with ethyl acetate, dried over MgSO4 and concentrated to give the title compound. This product is used without further purification. MS (ESI) 210 (M+H)+.

Workup

  1. temperatureThe resulting solution is cooled
  2. additionpoured into ice
  3. extractionThis mixture is extracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-912f867d2520451da7082637ac34dc85
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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