Bromopyruvic Acid → 2-(Ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid

HRID 2203096Notes

Reaction equation

HRID 2203096 reaction equation
[NH2:1][C:2](=[S:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[CH2:10][C:11](=O)[C:12]([OH:14])=[O:13]>C1COCC1>[CH2:6]([O:5][C:3]([C:2]1[S:8][CH:10]=[C:11]([C:12]([OH:14])=[O:13])[N:1]=1)=[O:4])[CH3:7]

Participants

4

Reactant 2

HCID 70684Bromopyruvic AcidHCID 2733398Ethyl thiooxamate

Product 1

HCID 534878632-(Ethoxycarbonyl)-1,3-thiazole-4-carboxylic acidYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 2-amino-2-thioxoacetate (10.1 g), 3-bromo-2-oxopropanoic acid (12.7 g) and THF (200 ml) was stirred at 50° C. overnight. The mixture was concentrated in vacuo, and the resulting solid was suspended in EtOAc. The precipitate was collected by filtration to give the title compound (7.4 g) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a66a0c4a3d2a46ff8b51d706f7b576c5
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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