Sodium Hydroxide → 2-Methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetic acid

HRID 444253Notes

Reaction equation

HRID 444253 reaction equation
[OH-].[Na+].[CH3:3][O:4][N:5]=[C:6]([C:12]1[N:13]=[N:14][S:15][CH:16]=1)[C:7]([O:9]CC)=[O:8]>O.CO>[CH3:3][O:4][N:5]=[C:6]([C:12]1[N:13]=[N:14][S:15][CH:16]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53899707Ethyl 2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetate

Product 1

HCID 543473402-Methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetic acidYield 71.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (0.47 g.) in water (10 ml.) was added to a solution of ethyl 2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetate (anti isomer) (2.1 g.) in methanol (20 ml.) and the resulting mixture was stirred for 6 hours at ambient temperature. Methanol was removed from the reaction mixture and to the residue was added water. The resulting mixture was washed with ether, adjusted to pH 1 with 10% hydrochloric acid and extracted twice with ether (50 ml.). The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off to give oil of 2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetic acid (anti isomer) (1.3 g.).

Workup

  1. customMethanol was removed from the reaction mixture and to the residue
  2. additionwas added water
  3. washThe resulting mixture was washed with ether
  4. extractionextracted twice with ether (50 ml.)
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-586f70e487b746f8a2c3499aa6168d4e
Source dataset
uspto-grants-1981_04
Patent number
US04263291

Reaction notes

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