Hydrochloric Acid → 2-(2-Aminothiazol-4-yl)-2-cyanomethoxyiminoacetic acid

HRID 1758386Notes

Reaction equation

HRID 1758386 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]#[N:17])[C:10]([OH:12])=[O:11])[N:8]=1)=O.Cl>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]#[N:17])[C:10]([OH:12])=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54179750HCID 54179750, compound

Product 1

HCID 544609212-(2-Aminothiazol-4-yl)-2-cyanomethoxyiminoacetic acidYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetic acid (syn isomer, 2.54 g) and conc. hydrochloric acid (3 ml) in methanol (30 ml) was stirred at room temperature for an hour. After removing methanol from the resultant mixture in vacuo, water was added to the residue and adjusted to pH 3.3 with an aqueous solution of sodium bicarbonate under ice-cooling. The precipitates were collected by filtration to give 2-(2-aminothiazol-4-yl)-2-cyanomethoxyiminoacetic acid (sym isomer, 2.1 g)

Workup

  1. customAfter removing methanol from the resultant mixture in vacuo, water
  2. additionwas added to the residue
  3. temperaturecooling
  4. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-52384be426be4c1b80bf5d798e4593b5
Source dataset
uspto-grants-1983_02
Patent number
US04372952

Reaction notes

Loading…