Sodium Hydroxide → 2-(2-Amino-4-thiazolyl)-2-ethoxyiminoacetic acid

HRID 648411Notes

Reaction equation

HRID 648411 reaction equation
C([O:3][C:4](=[O:16])[C:5](=[N:12][O:13][CH2:14][CH3:15])[C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)C.[OH-].[Na+]>C(O)C>[CH2:14]([O:13][N:12]=[C:5]([C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)[C:4]([OH:16])=[O:3])[CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53897917HCID 53897917, compound

Product 1

HCID 534242352-(2-Amino-4-thiazolyl)-2-ethoxyiminoacetic acidYield 65.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl-2-ethoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (5 g.) was added to a mixture of 1 N sodium hydroxide (45.9 ml.) and ethanol (30 ml.) and stirred at ambient temperature for 5 hours. After removing ethanol from the resultant solution under reduced pressure, the residue was dissolved in water (60 ml.) and adjusted to pH2.0 with 10% hydrochloric acid. The solution was subjected to salting-out, and the precipitates were collected by filtration and dried to give 2-ethoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetic acid (syn isomer) (2.9 g.).

Workup

  1. customAfter removing ethanol from the resultant solution under reduced pressure
  2. dissolutionthe residue was dissolved in water (60 ml.)
  3. filtrationthe precipitates were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-5e9e3577c6334649afe3110b94b06ec5
Source dataset
uspto-grants-1983_10
Patent number
US04411898

Reaction notes

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