Hydrochloric Acid → 2-(2-Aminothiazole-4-yl)-2-acetoxyiminoacetic acid

HRID 1815598Notes

Reaction equation

HRID 1815598 reaction equation
O.O.[Na+].[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:14][OH:15])[C:11]([O-:13])=[O:12])[N:9]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:14][O:15][C:16](=[O:18])[CH3:17])[C:11]([OH:13])=[O:12])[N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 74087995HCID 74087995, compound

Product 1

HCID 533948252-(2-Aminothiazole-4-yl)-2-acetoxyiminoacetic acidYield 103.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

2-(2-aminothiazole-4-yl)-2-hydroxyiminoacetate sodium dihydrate (syn-isomer) (24.6 g) was added to water (160 ml) and stirred at 20 to 30° C. Acetic anhydride (28.7 g) was added dropwise thereto for 60 minutes. During the dropwise addition, the pH of the mixture was controlled to 6.0±0.2 by using 20% aqueous sodium carbonate. After the dropwise addition, the mixture was stirred for 30 minutes, and the pH of the mixture was adjusted to 2.5 by using 6N hydrochloric acid. After the reaction liquid was cooled to 5° C., the precipitated crystal was filtered and washed with isopropanol and acetone successively. The obtained wet crystal was dried under reduced pressure to obtain 2-(2-aminothiazole-4-yl)-2-acetoxyiminoacetic acid (syn-isomer) (23.9 g) including two molecules of crystal water.

Workup

  1. additionDuring the dropwise addition
  2. additionAfter the dropwise addition
  3. stirringthe mixture was stirred for 30 minutes
  4. customAfter the reaction liquid
  5. temperaturewas cooled to 5° C.
  6. filtrationthe precipitated crystal was filtered
  7. washwashed with isopropanol and acetone successively
  8. customThe obtained wet crystal was dried under reduced pressure

Sources & evidence

ORD record
ord-b860408e1a044d9e9d83586e030fd2bf
Source dataset
uspto-grants-2005_04
Patent number
US06878827B2

Reaction notes

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