Sodium Bicarbonate → 2-(2-Formamidothiazol-4-yl)-2-[(3-isoxazolyl)methoxyimino]acetic acid

HRID 894759Notes

Reaction equation

HRID 894759 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=O)[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2].Cl.[O:15]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][NH2:22])=[N:16]1.C(=O)(O)[O-].[Na+]>O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:22][O:21][CH2:20][C:17]2[CH:18]=[CH:19][O:15][N:16]=2)[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 23315718(3-Isoxazolyl)methoxyamine hydrochloride

Product 1

HCID 537376352-(2-Formamidothiazol-4-yl)-2-[(3-isoxazolyl)methoxyimino]acetic acidYield 76.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-formamidothiazol-4-yl)glyoxylic acid (5 g.), (3-isoxazolyl)methoxyamine hydrochloride (4.53 g.), sodium bicarbonate (4.2 g.) and water (200 ml.) was stirred at room temperature for 4 hours, while keeping at pH 5.0. After removing the insoluble substance from the resultant mixture by filtration, the filtrate was adjusted to pH 1.5 with 10% hydrochloric acid and stirred at 5° C. for 30 minutes. The precipitates were collected by filtration, washed with water and dried to give 2-(2-formamidothiazol-4-yl)-2-[(3-isoxazolyl)methoxyimino]acetic acid (syn isomer, 5.68 g.), mp. 110° C. (dec.).

Workup

  1. customAfter removing the insoluble substance from the resultant mixture
  2. filtrationby filtration
  3. stirringstirred at 5° C. for 30 minutes
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-34d45bf7ed7243ed8bd61a01df9a07fb
Source dataset
uspto-grants-1981_08
Patent number
US04284631

Reaction notes

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