Hydrochloric Acid → 2-(2-Formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid

HRID 745377Notes

Reaction equation

HRID 745377 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=O)[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2].C(=O)(O)[O-].[Na+].[NH2:19][O:20][CH2:21][C:22]([NH2:24])=[O:23].Cl>O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:19][O:20][CH2:21][C:22](=[O:23])[NH2:24])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 139561842-(Aminooxy)acetamide

Product 1

HCID 538052302-(2-Formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acidYield 57.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(2-formamidothiazol-4-yl)-glyoxylic acid (4.63 g.) and sodium bicarbonate (1.95 g.) in water (230 ml.) was added 2-aminooxyacetamide (2.5 g.) and the mixture was stirred at room temperature for 6 hours while keeping at pH 5. After adjusting the solution to pH 1.5 with 10% hydrochloride acid, the precipitates were collected by filtration, washed with water and dried to give 2-(2-formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid (syn isomer, 3.6 g.), mp 195° C. (dec.).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-85762016d42e4a729e04ed77e4fbff96
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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