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

HRID 1278137Notes

Reaction equation

HRID 1278137 reaction equation
ON=[C:3]([C:9]1[N:10]=[C:11]([NH2:14])[S:12][CH:13]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([OH:17])C.S(=O)(O)[O-].[Na+]>O>[NH2:14][C:11]1[S:12][CH:13]=[C:9]([C:3](=[O:17])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6738988Ethyl 2-(2-aminothiazole-4-yl)-2-hydroxyiminoacetateHCID 23665763Sodium Bisulfite

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-hydroxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (a mixture of syn and anti isomers) (0.37 L g), ethanol (5 ml), water (5 ml) and sodium bisulfite (0.72 g) was stirred for 12 hours at 65° to 70° C. The reaction mixture was concentrated and water (10 ml) was added to the residue. The resulting mixture was subjected to salting-out and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated to give yellow crystals of ethyl 2-(2-amino-1,3-thiazol-4-yl)glyoxylate (0.18 g), mp 115° to 120° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (10 ml) was added to the residue
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c600e8e1896a498780f41b39667517a6
Source dataset
uspto-grants-1981_07
Patent number
US04279818

Reaction notes

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