Ethyl bromopyruvate → Ethyl 2-aminothiazole-4-carboxylate

HRID 408497Notes

Reaction equation

HRID 408497 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 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl bromopyruvate (100 g, 80% purity, 0.41 mol), thiourea (31 g, 0.41 mol) and ethanol (500 mL) was heated to reflux for 12 hours. The solvent was evaporated to dryness and the residue was washed with ether. The solid was suspended in a saturated aqueous solution of sodium bicarbonate (500 mL) for 30 minutes. The solid was filtered, washed with water, and dried over sodium sulfate to give 2-amino-thiazole-4-carboxylic acid ethyl ester (45 g, 0.26 mol, 63%) as an off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. customThe solvent was evaporated to dryness
  4. washthe residue was washed with ether
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-de4f6f345ca7410aac6b9bae4063f84a
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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