Methane → Ethyl 2-(2-Amino-4-thiazolyl)-2-oxoacetate

HRID 1534455Notes

Reaction equation

HRID 1534455 reaction equation
Br[CH2:2][C:3]([C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.[NH2:12][C:13]([NH2:15])=[S:14].C>O.C(O)C>[NH2:15][C:13]1[S:14][CH:2]=[C:3]([C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:12]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 2723790ThioureaHCID 13455954Ethyl bromoacetylglyoxylate

Product 1

HCID 4356513Ethyl 2-(2-Amino-4-thiazolyl)-2-oxoacetate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

195 g of ethyl bromoacetylglyoxylate are added dropwise to a solution of 66 g of thiourea in 450 ml of water and 450 ml of ethanol at 5° and after the addtion has ended, the mixture is stirred at room temperature for 30 minutes and at 50° for 30 minutes and, after adding active charcoal, the resulting reaction mixture is then filtered. The filtrate is brought to pH 7 by adding sodium bicarbonate solution, whereupon ethyl 2-amino-thiazol-4-ylglyoxylate crystallizes out in crystals of melting point 147°.

Workup

  1. customthe resulting reaction mixture
  2. filtrationis then filtered
  3. additionby adding sodium bicarbonate solution
  4. customwhereupon ethyl 2-amino-thiazol-4-ylglyoxylate crystallizes out in crystals of melting point 147°

Sources & evidence

ORD record
ord-584d795861f847919cb2a9c3bf72f228
Source dataset
uspto-grants-1992_02
Patent number
US05089490

Reaction notes

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