Malonic acid, bromoethyl-, diethyl ester → 5-Thiazolecarboxylic acid, 4-hydroxy-2-methyl-, ethyl ester

HRID 925274Notes

Reaction equation

HRID 925274 reaction equation
C(O[C:4](=[O:14])[C:5](CC)(Br)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[C:15]([NH2:18])(=[S:17])[CH3:16]>C1(C)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[S:17][C:15]([CH3:16])=[N:18][C:4]=1[OH:14])=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 141469Malonic acid, bromoethyl-, diethyl esterHCID 2723949Thioacetamide

Product 1

HCID 1357419865-Thiazolecarboxylic acid, 4-hydroxy-2-methyl-, ethyl esterYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 2-bromo-propanedioic acid diethyl ester (32.0 g, 133.2 mmol) and thioacetamide (10.0 g, 133.2 mmol) in toluene (130 ml) is refluxed for 4 h and then cooled. The insoluble material is filtered off and the filtrate is concentrated. The residue is suspended in diisopropyl ether and collected by filtration to give the 4-hydroxy-2-methyl-thiazole-5-carboxylic acid ethyl ester (7.2 g, 38.5 mmol, 29%).

Workup

  1. temperatureis refluxed for 4 h
  2. temperaturecooled
  3. filtrationThe insoluble material is filtered off
  4. concentrationthe filtrate is concentrated
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5dbf06f391604422b05bea8972f2cffa
Source dataset
uspto-grants-2016_03
Patent number
US09284286B2

Reaction notes

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