Hydrochloric Acid → 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetic acid

HRID 2286987Notes

Reaction equation

HRID 2286987 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:8]1[N:12]=[C:11]([NH:13]C=O)[S:10][N:9]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].Cl.[Cl-].[Na+]>>[CH3:1][O:2][N:3]=[C:4]([C:8]1[N:12]=[C:11]([NH2:13])[S:10][N:9]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 54428012HCID 54428012, compound

Product 1

HCID 533952072-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetic acidYield 73.2%

Procedure

A solution of 2-methoxyimino-2-(5-formamido-1,2,4-thiadiazol-3-yl)acetic acid (syn isomer) (1.4 g) in 1 N aqueous solution of sodium hydroxide (19.1 ml) was heated at 50° to 55° C. for an hour. To the solution was added conc. hydrochloric acid (1.9 ml) under cooling in an ice-bath. The mixture was saturated with sodium chloride and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was triturated with diethyl ether to give the title compound (0.9 g), mp. 180° to 182° C. (dec.).

Workup

  1. temperatureunder cooling in an ice-bath
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8da39600d44243a1a4999fec2617f340
Source dataset
uspto-grants-1981_05
Patent number
US04268509

Reaction notes

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