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

HRID 648393Notes

Reaction equation

HRID 648393 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]>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

4

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 67.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 N Aqueous solution of sodium hydroxide (6.7 ml.) was added to a solution of ethyl 2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetate (syn isomer) (1.2 g.) in methanol (10 ml.) and the mixture was stirred for 1.5 hours at ambient temperature. Methanol was distilled off from the reaction mixture and water was added to the residue. The mixture was washed with ether, adjusted to pH 1 with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off to give prisms of 2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetic acid (syn isomer) (0.7 g.), mp 110° to 113° C.

Workup

  1. distillationMethanol was distilled off from the reaction mixture and water
  2. additionwas added to the residue
  3. washThe mixture was washed with ether
  4. extractionextracted with ethyl acetate
  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-e80e0470312240a390f41b4c6fb27414
Source dataset
uspto-grants-1983_10
Patent number
US04411898

Reaction notes

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