Hydrochloric Acid → 2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetic acid

HRID 1381347Notes

Reaction equation

HRID 1381347 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:9]1[N:13]=[C:12]([NH:14]C=O)[S:11][N:10]=1)[C:6]([OH:8])=[O:7])[CH3:2].[OH-].[Na+].Cl>C(OCC)(=O)C>[CH2:1]([O:3][N:4]=[C:5]([C:9]1[N:13]=[C:12]([NH2:14])[S:11][N:10]=1)[C:6]([OH:8])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 537593012-Ethoxyimino-2-(5-formamido-1,2,4-thiadiazol-3-yl)acetic acid

Product 1

HCID 543509922-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetic acidYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-ethoxyimino-2-(5-formamido-1,2,4-thiadiazol-3-yl)acetic acid (syn isomer) (4.4 g) and 1N aqueous solution of sodium hydroxide (54 ml) was stirred for 2 hours at 50° to 55° C. The mixture was cooled in an ice bath, acidified with hydrochloric acid (5.4 ml) and extracred with ethyl acetate. The extract was dried over magnesium sulfate and evaporated to dryness. The residue was triturated with diethyl ether to give 2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetic acid (syn isomer) (2.92 g), mp. 168° to 170° C. (dec.).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. dry with materialThe extract was dried over magnesium sulfate
  3. customevaporated to dryness
  4. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-e8a7356b260347e1ba3d075c5bbb8d32
Source dataset
uspto-grants-1986_04
Patent number
US04585872

Reaction notes

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