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

HRID 1074343Notes

Reaction equation

HRID 1074343 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:13][O:14][CH:15]2[CH2:17][CH2:16]2)[C:8]([O:10]CC)=[O:9])[N:3]=1.Cl>[OH-].[Na+]>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:13][O:14][CH:15]2[CH2:17][CH2:16]2)[C:8]([OH:10])=[O:9])[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54418624Ethyl 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(cyclopropyloxyimino)acetate

Product 1

HCID 536571952-(5-Amino-1,2,4-thiadiazol-3-yl)-2-cyclopropyloxyiminoacetic acidYield 16.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of ethyl 2-(5-amino-l,2,4-thiadiazol-3-yl)-2-(cyclopropyloxyimino)acetate (syn isomer)(763 mg) in 1N sodium hydroxide (6 ml) was stirred at ambient temperature for 2 hours to give a clear solution. The mixture was adjusted to pH 4.5 with 1N hydrochloric acid and washed with ethyl acetate. The aqueous solution was adjusted to pH 3 with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and crystallized from diethyl ether to give 2-(5-amino-l,2,4-thiadiazol-3-yl)-2-cyclopropyloxyiminoacetic acid (syn isomer) (110 mg) as a crystal.

Workup

  1. customto give a clear solution
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-ab291c4d1d904fc7b51db7db061cd69e
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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