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

HRID 543832Notes

Reaction equation

HRID 543832 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 544280122-Methoxyimino-2-(5-formamido-1,2,4-thiadiazol-3-yl)acetic acid

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. additionTo the solution was added conc
  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-e78ee80d145c42a9ac37bc71abe7d8fa
Source dataset
uspto-grants-1984_05
Patent number
US04447429

Reaction notes

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