Sodium Bicarbonate → Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

HRID 463567Notes

Reaction equation

HRID 463567 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.Cl.[CH3:15][O:16][NH2:17].C(=O)([O-])O.[Na+]>C(O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:17][O:16][CH3:15])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 4356513Ethyl 2-(2-Amino-4-thiazolyl)-2-oxoacetate

Product 1

HCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

In 10 ml of 50% aqueous ethanol is dissolved 200 mg of ethyl 2-aminothiazol-4-yl-glyoxylate, followed by the addition of 166 mg of O-methylhydroxylamine hydrochloride and, then, 168 mg of sodium hydrogen carbonate. The mixture is stirred in a closed vessel at 70° C. for 5 hours. The reaction mixture is concentrated under reduced pressure and the residue is diluted with 10 ml of water and extracted with ethyl acetate. The ethyl acetate layer is washed with water and dried. The ethyl acetate is then distilled off to obtain ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate as crystals. Based on NMR and other data, this product is found to be an 83:17 mixture of syn- and anti-isomers.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionthe residue is diluted with 10 ml of water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer is washed with water
  5. customdried
  6. distillationThe ethyl acetate is then distilled off

Sources & evidence

ORD record
ord-a2aab2711f2c4cf9867a004cb38c8884
Source dataset
uspto-grants-1985_05
Patent number
US04520194

Reaction notes

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