Benzyl Bromide → HCID 660782, compound

HRID 1196222Notes

Reaction equation

HRID 1196222 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6](=[O:16])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)C>[C:24]1([CH2:23][N:3]2[CH:4]=[CH:5][C:6](=[O:16])[C:7]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:2]2[CH3:1])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27264163-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONE

Product 1

HCID 660782HCID 660782, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

73 g of the product of Example 2 were dissolved in 4 liters of ethanol (dry). 25 g K2CO3 powderized and 70 g benzylbromide were added. After refluxing for 4 hours and filtration, the solvent was distilled off and the residue extracted with 4 liters of hot petroleum ether in 3 parts. After cooling to room temperature and filtration the petroleum ether filtrate was concentrated to 2 liters and cooled to -10° C. 31 g of white crystals of the title compound of Example 3 were obtained. The formed title compound 3A was insoluble in petroleum ether at room temperature white crystals. 70% of total yield.

Workup

  1. temperatureAfter refluxing for 4 hours
  2. filtrationfiltration
  3. distillationthe solvent was distilled off
  4. extractionthe residue extracted with 4 liters of hot petroleum ether in 3 parts
  5. filtrationfiltration the petroleum ether filtrate
  6. concentrationwas concentrated to 2 liters
  7. temperaturecooled to -10° C

Sources & evidence

ORD record
ord-d876cc6cf7f642e888cb9df70caed447
Source dataset
uspto-grants-1992_05
Patent number
US05112968

Reaction notes

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