Diethyl bromomalonate → 5-Thiazolecarboxylic acid, 4-hydroxy-2-methyl-, ethyl ester

HRID 1365839Notes

Reaction equation

HRID 1365839 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].Br[CH:6]([C:12](OCC)=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C1(C)C=CC=CC=1>[CH2:10]([O:9][C:7]([C:6]1[S:3][C:1]([CH3:2])=[N:4][C:12]=1[OH:13])=[O:8])[CH3:11]

Participants

4

Reactant 2

HCID 69637Diethyl bromomalonateHCID 2723949Thioacetamide

Product 1

HCID 1357419865-Thiazolecarboxylic acid, 4-hydroxy-2-methyl-, ethyl esterYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of thioacetamide (17.2 g, 0.229 mol) in toluene (130 mL) was added diethyl bromomalonate (55.0 g, 0.230 mol) and the mixture heated at reflux for 3 h. The reaction mixture was cooled to RT, filtered through Celite, then concentrated in vacuo. The resultant solid was triturated with hexane to give the title compound as a yellow solid (11.0 g, 26%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 h
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo
  5. customThe resultant solid was triturated with hexane

Sources & evidence

ORD record
ord-a8c5f6480d2d42cc9651a9312b388a40
Source dataset
uspto-grants-2011_02
Patent number
US07893060B2

Reaction notes

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