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

HRID 1246437Notes

Reaction equation

HRID 1246437 reaction equation
[Br:1][CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:10][C:11]([NH2:13])=[S:12]>C(O)C>[BrH:1].[NH2:13][C:11]1[S:12][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:10]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2723790Thiourea

Product 1

HCID 16495520Ethyl 2-aminothiazole-4-carboxylate hydrobromideYield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-bromo-2-oxopropanoate (100 g), thiourea (39 g) and ethanol (500 ml) was refluxed for 2 hours. The reaction mixture was concentrated in vacuo. The crystalline residue was collected and washed with ethyl acetate to give ethyl 2-amino-1,3-thiazole-4-carboxylate hydrobromide (116 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe crystalline residue was collected
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-5e55cb4cb8894543824c526db6b5de81
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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