Thioacetamide → Methyl 2-methyl-1,3-thiazole-5-carboxylate

HRID 1919572Notes

Reaction equation

HRID 1919572 reaction equation
[CH:1]([CH:3](Cl)[C:4]([O:6][CH3:7])=[O:5])=O.[C:9]([NH2:12])(=[S:11])[CH3:10]>O>[CH3:10][C:9]1[S:11][C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:1][N:12]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 14355182Methyl 2-chloro-3-oxopropanoate

Product 1

HCID 21427465Methyl 2-methyl-1,3-thiazole-5-carboxylateYield 43.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.0 g (14.6 mmol) methyl formylchloroacetate (A. Gangjee, A. Vidwans, E. Elzein, et. Al. J. Med. Chem. 2001, 44, 1993-2003), and 1.6 g (21.3 mmol) thioacetamide were dissolved in 10 ml water, heated, and reacted at 95° C. for 5 hr. The reaction product was extracted with ethyl acetate for 3 times, the ethyl acetate phases were combined, washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by a column chromatography to obtain 1.0 g methyl 2-methylthiazol-5-carboxylate (yield 43%), 1H NMR (CDCl3) 2.76 (3H, s), 3.89 (3H, s), 8.25 (1H, s).

Workup

  1. temperatureheated
  2. customreacted at 95° C. for 5 hr
  3. extractionThe reaction product was extracted with ethyl acetate for 3 times
  4. washwashed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customseparated by a column chromatography

Sources & evidence

ORD record
ord-aa214b6c6d174096a9f64c8cd4bbda1f
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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