Benzyl Chloride → 1-Benzyl-5-fluoropyrimid-2-one

HRID 1075152

Reaction equation

HRID 1075152 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].[F:10][C:11]1[CH:12]=[N:13][C:14](=[O:17])[NH:15][CH:16]=1>CN(C)C=O>[CH2:1]([N:15]1[CH:16]=[C:11]([F:10])[CH:12]=[N:13][C:14]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 1014985-Fluoropyrimidin-2-oneHCID 5462222Potassium

Product 1

HCID 136163371-Benzyl-5-fluoropyrimid-2-oneYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl chloride (0.01 mol) was added to a stirred mixture of the potassium salt of 5-fluoropyrimid-2-one (0.007 mol) in dimethylformamide (40 ml) and the mixture stirred at room temperature until chromatography showed the reaction to be complete. The solvent was then evaporated at reduced presure (1 mm Hg) and the residue was extracted with chloroform (100 ml). The chloroform solution was washed with aqueous 2 N NaCH (2×3 ml) and with water (3 ml) before drying (MgSO4) and evaporation; yield 50%, m.p. 163° C. (ethyl actate). (Found: C, 64.69; H, 4.49. Calc. for C11H9FN2O: C, 64.70; H, 4.44).

Workup

  1. customthe reaction
  2. customThe solvent was then evaporated at reduced presure (1 mm Hg)
  3. extractionthe residue was extracted with chloroform (100 ml)
  4. washThe chloroform solution was washed with aqueous 2 N NaCH (2×3 ml) and with water (3 ml)
  5. custombefore drying
  6. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-d93c328bdab04733b4b8c1df95d2c388
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Linked notes

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