Hydrochloric Acid → 2-Allyloxyimino-2-(2-formamidothiazol-4-yl)acetic acid

HRID 904870Notes

Reaction equation

HRID 904870 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+].Cl.[CH2:20]([O:23][NH2:24])[CH:21]=[CH2:22].Cl>O.C(OCC)(=O)C>[CH2:20]([O:23][N:24]=[C:9]([C:7]1[N:8]=[C:4]([NH:3][CH:1]=[O:2])[S:5][CH:6]=1)[C:10]([OH:12])=[O:11])[CH:21]=[CH2:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acid

Product 1

HCID 542025522-Allyloxyimino-2-(2-formamidothiazol-4-yl)acetic acidYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-formamidothiazol-4-yl)-glyoxylic acid (30 g) and sodium bicarbonate (12.6 g) in water (1300 ml) was added allyloxyamine hydrochloride (19.8 g), and the mixture was stirred for 7 hours at ambient temperature at pH 6. To the reaction mixture was added ethyl acetate (500 ml). After the mixture was adjusted to pH 1.9 with 10% hydrochloric acid, the ethyl acetate layer was separated. The ethyl acetate layer was washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and then the solvent was distilled off. The residue was pulverized in diisopropyl ether, collected by filtration and then dried to give 2-allyloxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (25.3 g).

Workup

  1. customthe ethyl acetate layer was separated
  2. washThe ethyl acetate layer was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-30557d8850204dc1a5908fcfdfc7c8af
Source dataset
uspto-grants-1983_12
Patent number
US04420477

Reaction notes

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