Phenethyl bromide → 4-phenyl-2-(2-phenylethyl)-1(2H)-phthalazinone

HRID 54970Notes

Reaction equation

HRID 54970 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].Br[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[Na+]>CS(C)=O.O>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 7666Phenethyl bromideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 2191504-Phenyl-1-(2H)-phthalazinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 7227954-phenyl-2-(2-phenylethyl)-1(2H)-phthalazinoneYield 95.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Eighty-five grams (0.38 moles) of 4-phenyl-1(2H)-phthalazinone was added to 18.4 g (0.47 moles) of sodium hydride in 1 L of DMSO in four portions. The mixture was stirred for two hours at room temperature until evolution of hydrogen had ceased, and 95.5 g (0.52 moles) of 2-bromoethylbenzene was added. The mixture was stirred 1.5 hours at room temperature, 1 L of 2N NaOH was added and the slurry was poured into 1 L of water. The product was filtered off and dried to yield 118 g (95%) of 4-phenyl-2-(2-phenylethyl)-1(2H)-phthalazinone, mp 135-138.

Workup

  1. filtrationThe product was filtered off
  2. customdried

Sources & evidence

ORD record
ord-94ea99dcbbe542119c1f3db607b380b9
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Reaction notes

Loading…