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

HRID 1447269Notes

Reaction equation

HRID 1447269 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-b7f954546b5741178e347cb80f0e23fc
Source dataset
uspto-grants-1982_02
Patent number
US04316019

Reaction notes

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