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

HRID 1421948

Reaction equation

HRID 1421948 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:12]([NH2:14])=[S:13]>C(O)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:12]2[S:13][CH:5]=[C:3]([CH2:2][Cl:1])[N:14]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH3:19]

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 27584903,4-Dimethoxythiobenzamide

Product 1

HCID 20793964-(Chloromethyl)-2-(3,4-dimethoxyphenyl)-1,3-thiazoleYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.5 g of 1,3-dichloroacetone and 2.3 g of 3,4-dimethoxythiobenzamide were suspended in 100 ml of ethanol. The suspension was heated for 3 hours to complete the reaction. The solvent was removed by distillation. The residue was purified by silica gel column chromatography to obtain 1.86 g of 2-(3,4-dimethoxyphenyl)-4-chloromethylthiazole as a colorless viscous oil.

Workup

  1. temperatureThe suspension was heated for 3 hours
  2. customthe reaction
  3. customThe solvent was removed by distillation
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5498671472d94442b51712a9af07884e
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Linked notes

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