Ethyl bromopyruvate → Ethyl 2-aminothiazole-4-carboxylate hydrobromide

HRID 2053159Notes

Reaction equation

HRID 2053159 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[Br:5][CH2:6][C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9]>CC(C)=O>[BrH:5].[CH2:11]([O:10][C:8]([C:7]1[N:1]=[C:2]([NH2:4])[S:3][CH:6]=1)=[O:9])[CH3:12]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2723790Thiourea

Product 1

HCID 16495520Ethyl 2-aminothiazole-4-carboxylate hydrobromideYield 52%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Thiourea (1.5 g, 20 mmol) and ethyl bromopyruvate (2.8 ml, 22 mmol) were heated at 100° C. for 1 h. The reaction was cooled and acetone (10 ml) was added. The mixture was then filtered to give a yellow/brown solid and the crude material was crystallised from hot ethanol (20 ml) to give the title compound as the HBr salt (2.63 g). The liquor was concentrated and recrystallised from hot EtOH (5 ml) to give further product (0.63 g).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationThe mixture was then filtered
  3. customto give a yellow/brown solid
  4. customthe crude material was crystallised from hot ethanol (20 ml)

Sources & evidence

ORD record
ord-5120e5c885ba49bf9c6130248b40c262
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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