Thioacetamide → Methyl 2-methyl-1,3-thiazole-4-carboxylate

HRID 425772Notes

Reaction equation

HRID 425772 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].[CH3:5][O:6][C:7](=[O:12])[C:8](=O)[CH2:9]Cl>CC#N>[CH3:5][O:6][C:7]([C:8]1[N:4]=[C:1]([CH3:2])[S:3][CH:9]=1)=[O:12]

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 12530121Methyl 3-chloro-2-oxopropanoate

Product 1

HCID 14812829Methyl 2-methyl-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of thioacetamide (132 mmol, 1.0 eq) in MeCN (250 mL) is added to a mixture of the respective 3-chloro-2-oxo-propionic acid methyl ester derivative (132 mmol, 1.0 eq) and molecular sieves (4 Å, 12 g) in MeCN (60 mL). After stirring for 5 h the mixture is cooled in an ice-bath and the obtained precipitate is filtered off. The residue is washed with cold MeCN, dried, dissolved in MeOH (280 mL) and stirred at 50° C. for 6 h. The solvents are removed in vacuo to give the corresponding 2-methyl-thiazole-4-carboxylic acid methyl ester derivatives.

Workup

  1. temperatureis cooled in an ice-bath
  2. filtrationthe obtained precipitate is filtered off
  3. washThe residue is washed with cold MeCN
  4. customdried
  5. dissolutiondissolved in MeOH (280 mL)
  6. stirringstirred at 50° C. for 6 h
  7. customThe solvents are removed in vacuo

Sources & evidence

ORD record
ord-f5dfc948f7ab40e9a206080a55578619
Source dataset
uspto-grants-2012_01
Patent number
US08106215B2

Reaction notes

Loading…