1,3-Dichloroacetone → 4-chloromethyl-2-[(E)-styryl]thiazole

HRID 1584327Notes

Reaction equation

HRID 1584327 reaction equation
[C:1]([NH2:11])(=[S:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:12][CH2:13][C:14]([CH2:16]Cl)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:12][CH2:13][C:14]1[N:11]=[C:1](/[CH:2]=[CH:3]/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[S:10][CH:16]=1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 11430Potassium CarbonateHCID 538788953-Phenylprop-2-enethioamide

Product 1

HCID 220097354-chloromethyl-2-[(E)-styryl]thiazoleYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of thiocinnamamide (11.7 g), 1,3-dichloro-acetone (9.1 g) and ethanol (145 ml) was stirred for one hour under reflux. The reaction mixture was poured into ice-water, which was neutralized with potassium carbonate, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The concentrate was purified by means of column chromatography on silica gel. From the fraction eluted with ether-hexane (1:6, v/v), was obtained 4-chloromethyl-2-[(E)-styryl]thiazole (9.4 g, 56%), which was recrystallized from ether-hexane to yield colorless plates, m.p.88-89° C.

Workup

  1. temperatureunder reflux
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of column chromatography on silica gel
  7. washFrom the fraction eluted with ether-hexane (1:6, v/v)

Sources & evidence

ORD record
ord-d6c2c8f14bb24d0b9543d65241db4238
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

Loading…