Sodium Bicarbonate → HCID 136025193, compound

HRID 1656160Notes

Reaction equation

HRID 1656160 reaction equation
[CH:1]([NH:3][C:4]1[S:5][C:6]([C:9](=O)[C:10]([OH:12])=[O:11])=[CH:7][N:8]=1)=[O:2].Cl.[O:15]([NH2:17])[CH3:16].C(=O)(O)[O-].[Na+]>O>[CH:1]([NH:3][C:4]1[S:5][C:6]([C:9](=[N:17][O:15][CH3:16])[C:10]([OH:12])=[O:11])=[CH:7][N:8]=1)=[O:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 19790069(2-Formamidothiazol-5-yl)glyoxylic acid

Product 1

HCID 136025193HCID 136025193, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of (2-formamidothiazol-5yl)glyoxylic acid (2.4 g) and methoxylamine hydrochloride (5.0 g) in water (144 ml) was adjusted to pH 4.9-5.0 with a saturated aqueous sodium bicarbonate and the mixture was stirred at ambient temperature for 4.7 hours. After water was added thereto in order to dissolve the insoluble material therein, the aqueous solution was concentrated to a volume of 100 ml. The precipitated material was collected by filtration, washed with water, followed by dissolving in a mixture of tetrahydrofuran and water. This solution was poured into a mixture of ethyl acetate and water, and the organic layer was separated out. After the aqueous solution was extracted with ethyl acetate, the combined ethyl acetate solution was washed with an aqueous sodium chloride and then dried over anhydrous magnesium sulfate. Removal of the solvent gave 2-(2-formamidothiazol-5-yl)-2-methoxyiminoacetic acid (anti isomer) (0.9 g), mp 159° C. (dec.). The filtrate obtained above was further concentrated to a volume of 70 ml, and the precipitated material was collected by filtration to recover the same product (0.23 g). Total yield: 1.13 g.

Workup

  1. dissolutionin order to dissolve the insoluble material
  2. concentrationthe aqueous solution was concentrated to a volume of 100 ml
  3. filtrationThe precipitated material was collected by filtration
  4. washwashed with water
  5. dissolutionby dissolving in a mixture of tetrahydrofuran and water
  6. additionThis solution was poured into a mixture of ethyl acetate and water
  7. customthe organic layer was separated out
  8. extractionAfter the aqueous solution was extracted with ethyl acetate
  9. washthe combined ethyl acetate solution was washed with an aqueous sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customRemoval of the solvent

Sources & evidence

ORD record
ord-dbde7699ae224948946e511730b25d41
Source dataset
uspto-grants-1993_10
Patent number
US05252731

Reaction notes

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