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

HRID 501823

Reaction equation

HRID 501823 reaction equation
[C:1](=[S:4])([NH2:3])[CH3:2].Br[CH2:6][C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(OCC)(=O)C.O>C(O)C>[CH3:2][C:1]1[S:4][CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 66144Ethyl bromopyruvateHCID 2723949Thioacetamide

Product 1

HCID 293353Ethyl 2-methyl-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.00 g of ethanethioamide was suspended in 50 mL of ethanol, to which 9.3 mL of ethyl 3-bromo-2-oxopropanoate was added dropwise at room temperature, and this suspension was stirred for one hour while heating it under reflux. The reaction mixture was cooled to room temperature and added to a mixture of ethyl acetate and water, followed by separation of the organic phase therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 2.30 g of ethyl 2-methyl-1,3-thiazole-4-carboxylate as white solid.

Workup

  1. additionwas added dropwise at room temperature
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. customfollowed by separation of the organic phase
  5. washAfter the resultant organic phase was washed with water
  6. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-3e4f7b4a41df49049212ab0dd143a4e6
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Linked notes

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