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

HRID 1723585Notes

Reaction equation

HRID 1723585 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-1,2,4-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 aqueus sodium chloride, dried over magnesium sulfate, and crystallized from diethyl ether to give 2-(5-amino-1,2,4-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 aqueus sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-afafda1f06fe44afa0417d0db0f6f2f3
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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