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

HRID 1107682Notes

Reaction equation

HRID 1107682 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>CO>[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 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.33 g of thiobenzamide was dissolved in 20 ml of dry methanol, and 2.16 g of 1,3-dichloroacetone was added thereto at room temperature and then heated under reflux for 1 hour. The solvent was distilled off under reduced pressure, and ice water was added to the remaining product, which was then neutralized with an aqueous solution of sodium hydrogen carbonate. The resulting product was extracted with ethyl acetate, washed with saturated saline, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 2.03 g of 4-chloromethyl-2-phenylthiazole was obtained from the fraction eluted with chloroform/n-hexane=1/2.

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationThe solvent was distilled off under reduced pressure, and ice water
  3. additionwas added to the remaining product, which
  4. extractionThe resulting product was extracted with ethyl acetate
  5. washwashed with saturated saline
  6. dry with materialdried over sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residual product was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-fa5f84e32bd74bcbaa1ce2493f116548
Source dataset
uspto-grants-2000_05
Patent number
US06063734

Reaction notes

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