Ethyl bromopyruvate → Ethyl 2-aminothiazole-4-carboxylate

HRID 2394919Notes

Reaction equation

HRID 2394919 reaction equation
Br[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>[CH2:7]([O:6][C:4]([C:3]1[N:10]=[C:11]([NH2:13])[S:12][CH:2]=1)=[O:5])[CH3:8]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2723790Thiourea

Product 1

HCID 73216Ethyl 2-aminothiazole-4-carboxylateYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 90% ethyl bromopyruvate (54.2 g, 0.25 mol) and thiourea (20 g, 0.263 mol) in 500 mL absolute ethanol was heated at reflux for 1 h and then stirred at ambient temperature for 2 h. Ethanol was removed in vacuo and the residue was suspended in ice-water and neutralized with solid potassium carbonate until basic. The solid was filtered, washed thoroughly with water and air-dried to give 42 g of ethyl-2-amino-4-thiazolecarboxylate.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customEthanol was removed in vacuo
  4. filtrationThe solid was filtered
  5. washwashed thoroughly with water
  6. customair-dried

Sources & evidence

ORD record
ord-205b8b87f28c4394bd87913109b3cc96
Source dataset
uspto-grants-1998_09
Patent number
US05811411

Reaction notes

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