Ethyl 2-chloroacetoacetate → Ethyl 4-methyl-2-sulfanyl-1,3-thiazole-5-carboxylate

HRID 550535Notes

Reaction equation

HRID 550535 reaction equation
Cl[CH:2]([C:8]([CH3:10])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:11](=[S:14])([S-:13])[NH2:12].[NH4+]>C(O)C>[CH3:10][C:8]1[NH:12][C:11](=[S:13])[S:14][C:2]=1[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 11083854Ammonium dithiocarbamate

Product 1

HCID 3957801Ethyl 4-methyl-2-sulfanyl-1,3-thiazole-5-carboxylateYield 40.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-chloroacetoacetate (5 g) and ammonium dithiocarbamate (3.37 g, prepared as reported in Synthesis (1985), (10), 948-9) in ethanol (20 mL) was refluxed overnight. The solvent was evaporated under vacuum and the crude product purified by flash chromatography on silica gel (eluting with cyclohexane:ethyl acetate from 1:0 to 7:3) to give the title compound (2.5 g). MS (m/z): 204 [MH]+.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe crude product purified by flash chromatography on silica gel (eluting with cyclohexane:ethyl acetate from 1:0 to 7:3)

Sources & evidence

ORD record
ord-507a6e1ea1b643dda63bcf012469fc5e
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Reaction notes

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