Water → HCID 15480821, compound

HRID 1857357Notes

Reaction equation

HRID 1857357 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:8][C:9]([CH2:11][N:12]1[C:17]([CH3:18])=[CH:16][N:15]=[C:14](O)[C:13]1=[O:20])=[O:10])[CH3:7].O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:3][C:14]1[C:13](=[O:20])[N:12]([CH2:11][C:9]([O:8][CH2:6][CH3:7])=[O:10])[C:17]([CH3:18])=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 178472615HCID 178472615, compound

Product 1

HCID 15480821HCID 15480821, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

PHOSPHOROUS OXYCHLORIDE (2.8 ML, 30 MMOL) WAS ADDED TO A STIRRED MIXTURE OF 1-ETHOXYCARBONYLMETHYL-3-HYDROXY-6-METHYLPYRAZINONE (5.3 G, 25 MMOL) IN DRY TOLUENE (50 ML) UNDER ARGON. THE RESULTING MIXTURE WAS HEATED TO 60° C. AFTER 64 H, THE MIXTURE WAS COOLED AND WATER AND ETHYL ACETATE WERE ADDED. THE ORGANIC LAYER WAS DRIED (NA2SO4) AND EVAPORATED IN VACUO. THE RESIDUE WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (50% ETOAC/HEXANES) TO GIVE THE TITLE COMPOUND AS A CRYSTALLINE SOLID:

Workup

  1. temperatureAFTER 64 H, THE MIXTURE WAS COOLED
  2. customTHE ORGANIC LAYER WAS DRIED (NA2SO4)
  3. customEVAPORATED IN VACUO
  4. customTHE RESIDUE WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (50% ETOAC/HEXANES)

Sources & evidence

ORD record
ord-7039d1eb607a4b00aa331d501fec1ffd
Source dataset
uspto-grants-2000_11
Patent number
US06147078

Reaction notes

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