Sodium Carbonate → 3-chloro-1-(4-fluorophenyl)pyrazin-2(1H)-one

HRID 2046176Notes

Reaction equation

HRID 2046176 reaction equation
P(Cl)(Cl)([Cl:3])=O.C1(O[C:13]2[C:14](=[O:26])[N:15]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:16]=[CH:17][N:18]=2)CCCCC1.C([O-])([O-])=O.[Na+].[Na+]>ClCCCl>[Cl:3][C:13]1[C:14](=[O:26])[N:15]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:16]=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 679759613-cyclohexyloxy-1-(4-fluoro-phenyl)-1H-pyrazin-2-one

Product 1

HCID 672214163-chloro-1-(4-fluorophenyl)pyrazin-2(1H)-oneYield 95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
160 °C

Procedure

Phosphorus oxychloride (0.94 mL, 10 mmol) was added to a solution of 3-cyclohexyloxy-1-(4-fluoro-phenyl)-1H-pyrazin-2-one (0.97 g, 3.36 mmol) in DCE (10 mL). The reaction mixture was stirred at 160° C. for 15 minutes under microwave irradiation. The reaction was poured into ice-water, then basified with a saturated solution of Na2CO3 and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 3-chloro-1-(4-fluoro-phenyl)-1H-pyrazin-2-one (0.71 g, 95% yield) that was used in the next step without further purification.

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-ea9224185cfa4a19aac0c6377e8e4691
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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