Sodium Bicarbonate → 2-(2-Formamidothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)acetic acid

HRID 1659796Notes

Reaction equation

HRID 1659796 reaction equation
P(O)(O)(O)=O.[Br:6][C:7]1[CH:15]=[CH:14][C:10]([CH2:11][O:12][NH2:13])=[CH:9][C:8]=1[OH:16].C(=O)(O)[O-].[Na+].[CH:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=O)[C:31]([OH:33])=[O:32])[N:29]=1)=[O:23]>O.C(O)C>[CH:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=[N:13][O:12][CH2:11][C:10]2[CH:14]=[CH:15][C:7]([Br:6])=[C:8]([OH:16])[CH:9]=2)[C:31]([OH:33])=[O:32])[N:29]=1)=[O:23]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 236167634-Bromo-3-hydroxybenzyloxyamine phosphate

Product 1

HCID 540633902-(2-Formamidothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)acetic acidYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The solution of 4-bromo-3-hydroxybenzyloxyamine phosphate (17.4 g.) in water (200 ml.) and ethanol (200 ml.) was stirred at room temperature and adjusted to pH 7.0 with sodium bicarbonate. 2-(2-Formamidothiazol-4-yl)glyoxylic acid (10.0 g.) was added to the solution and the resulting suspension was adjusted to pH 4.0 to 4.5. After stirring the solution at room temperature for 2 hours, ethanol was removed from the resultant solution in vacuo. Ethyl acetate was added to aqueous residue and adjusted to pH 2.5 with 10% hydrochloric acid. The ethyl acetate layer was separated, washed with water and dried over magnesium sulfate. The solution was concentrated in vacuo to give 2-(2-formamidothiazol-4-yl)-2-(4-bromo-3-hydroxybenzyloxyimino)acetic acid (syn isomer, 14.8 g.).

Workup

  1. customethanol was removed from the resultant solution in vacuo
  2. additionEthyl acetate was added to aqueous residue
  3. customThe ethyl acetate layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-a90fa862ff1745708ebd04c313029a66
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

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