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

HRID 322268Notes

Reaction equation

HRID 322268 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 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of thiocinnamamide (11.7 g), 1,3-dichloroacetone (9.10 g) and ethanol (145 ml) was heated for one hour under reflux. The reaction mixture was poured onto ice-water, neutralized with potassium carbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with diethyl ether-hexane (1:5, v/v), 4-chloromethyl-2-[(E)-2-phenylethenyl]thiazole (9.40 g, 66%) was obtained. Recrystallization from diethyl ether-hexane gave colorless plates, mp 88-89° C.

Workup

  1. temperaturewas heated for one hour
  2. temperatureunder reflux
  3. additionThe reaction mixture was poured onto ice-water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. washFrom the fraction eluted with diethyl ether-hexane (1:5

Sources & evidence

ORD record
ord-45a145d6c1eb42a384c8c44260b3e71e
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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