Magnesium Hydroxide → 2-Hydroxyimino-2-(isothiazol-4-yl)acetic acid

HRID 444266Notes

Reaction equation

HRID 444266 reaction equation
[S:1]1[CH:5]=[C:4]([C:6](=O)[C:7]([OH:9])=[O:8])[CH:3]=[N:2]1.[OH-:11].[Mg+2].[OH-].Cl.[NH2:15]O>C(O)C.O>[OH:11][N:15]=[C:6]([C:4]1[CH:3]=[N:2][S:1][CH:5]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 73981Magnesium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 129065552-(Isothiazol-4-yl)glyoxylic acid

Product 1

HCID 571550852-Hydroxyimino-2-(isothiazol-4-yl)acetic acidYield 76.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 2-(isothiazol-4-yl)glyoxylic acid (240 mg.), magnesium hydroxide (290 mg.) and hydroxylamine hydrochloride (140 mg.) in a mixture of ethanol (2 ml.) and water (10 ml.) was stirred for 2 hours at ambient temperature and allowed to stand overnight at ambient temperature. Ethanol was distilled off and to the residue was added ethyl acetate. The mixture was adjusted to pH 1 with 10% hydrochloric acid and the ethyl acetate layer was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give 2-hydroxyimino-2-(isothiazol-4-yl)acetic acid (syn isomer) (0.20 g.), mp 159° to 161° C. (dec.).

Workup

  1. waitto stand overnight at ambient temperature
  2. distillationEthanol was distilled off and to the residue
  3. additionwas added ethyl acetate
  4. washthe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-efe0bed4003d4d689bbe41b9de531366
Source dataset
uspto-grants-1981_04
Patent number
US04263291

Reaction notes

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