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

HRID 1406291

Reaction equation

HRID 1406291 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].[NH2:6][C:7](=[S:12])[C:8]([O:10][CH3:11])=[O:9].[CH3:13]CO>>[CH3:2][C:3]1[N:6]=[C:7]([C:8]([O:10][CH2:11][CH3:13])=[O:9])[S:12][CH:4]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6571ChloroacetoneHCID 15586167Methyl carbamothioylformate

Product 1

HCID 567306Ethyl 4-methyl-1,3-thiazole-2-carboxylateYield 33.8%

Conditions

Temperature
80 °C

Procedure

1-Chloropropan-2-one (0.334 mL, 4.20 mmol) and methyl 2-amino-2-thioxoacetate (500 mg, 4.20 mmol) was dissolved in EtOH. The reaction solution was heated to 80° C. for overnight, cooled to RT, concentrated and purified with a silica gel column by ISCO CombiFlash® chromatography eluting with 10%-35% EtOAc/Haptane to give the title compound as a yellowish oil (243 mg, 33.8%) as the ethyl ester. A methyl ester product was isolated as a yellow solid (104 mg, 15.8%).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated
  3. custompurified with a silica gel column by ISCO CombiFlash® chromatography
  4. washeluting with 10%-35% EtOAc/Haptane

Sources & evidence

ORD record
ord-02251b49e07348e5b1c9daea4076245c
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Linked notes

Loading…