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

HRID 2351197Notes

Reaction equation

HRID 2351197 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 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-21f93bfeb345491e891f9090c7239f27
Source dataset
uspto-grants-1989_10
Patent number
US04871860

Reaction notes

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