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

HRID 1717037Notes

Reaction equation

HRID 1717037 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-baf642a7a4864febac0eac66fb8c8300
Source dataset
uspto-grants-2010_09
Patent number
US07803841B2

Reaction notes

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