Chloroacetone → Ethyl 4-methyl-1,3-thiazole-2-carboxylate

HRID 967736Notes

Reaction equation

HRID 967736 reaction equation
[C:1](OCC)(=[S:5])[C:2]([NH2:4])=O.Cl[CH2:10]C(=O)C.CCCCCC.[C:20]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:21]>C(O)C>[CH3:10][C:2]1[N:4]=[C:21]([C:20]([O:23][CH2:24][CH3:25])=[O:22])[S:5][CH:1]=1

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 8058HexaneHCID 8857Ethyl AcetateHCID 216137632-ethoxy-2-thioxoAcetamide

Product 1

HCID 567306Ethyl 4-methyl-1,3-thiazole-2-carboxylateYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl thiooxamate (3.0 g, 22 mmol) was dissolved in ethanol (30 mL) under argon. Chloroacetone (1.8 mL, 22 mmol) was added and the resultant solution was heated at 80° C. for 16 h. The reaction mixture was concentrated in vacuo, adsorbed onto silica gel, and purified by column chromatography on silica gel eluting with 97:3, then 95:5 hexane:ethyl acetate to afford ethyl 4-methyl-1,3-thiazole-2-carboxylate (850 mg, 22% yield) as an oil. 1H NMR (CDCl3, 300 MHz) 7.20 (s, 1H), 4.48 (q, J=7.1 Hz), 2.56 (s, 3H), 1.47 (s, 3H). MS (EI ionization) 171 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography on silica gel eluting with 97:3

Sources & evidence

ORD record
ord-7e12347167a949b9897dc702b39f38aa
Source dataset
uspto-grants-2005_10
Patent number
US06956049B1

Reaction notes

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