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

HRID 1577741Notes

Reaction equation

HRID 1577741 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:11]1[N:12]=[C:13]([NH2:16])[S:14][CH:15]=1)[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][N:4]=[C:5]([C:11]1[N:12]=[C:13]([NH2:16])[S:14][CH:15]=1)[C:6]([OH:8])=[O:7])[CH3:2]

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 pH 2.0 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-1aad0be0f796473686af1995e1e930ae
Source dataset
uspto-grants-1981_09
Patent number
US04288436

Reaction notes

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