Benzoyl chloride → N-(1-oxo-4-phenyl-(2H)-phthalazin-2-yl)benzamide

HRID 567718Notes

Reaction equation

HRID 567718 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:18].C([O-])(O)=O.[Na+].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[O:18]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:11][N:2]1[NH:1][C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 212625372-amino-4-phenylphthalazin-1(2H)-one

Product 1

HCID 13010237N-(1-oxo-4-phenyl-(2H)-phthalazin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The general procedures described in Example 14, parts A and B are followed. The obtained 2-amino-4-phenyl-(2H)-1-phthalazinone (0.01 mol) is stirred with aqueous NaHCO3 and benzoylchloride (0.01 mol) in dichloromethane at room temperature overnight. The organic phase is washed with water, dried over Na2SO4 and dichloromethane is evaporated. The product is recrystallized to yield the title compound, N-(1-oxo-4-phenyl-(2H)-phthalazin-2-yl)benzamide (R1=benzyl, Y1=NH—C(O), R2=phenyl, A=phenyl, m=0, p=0).

Workup

  1. washThe organic phase is washed with water
  2. dry with materialdried over Na2SO4 and dichloromethane
  3. customis evaporated
  4. customThe product is recrystallized

Sources & evidence

ORD record
ord-61316335ecea41a4920f8b65f92a8558
Source dataset
uspto-grants-2001_01
Patent number
US06180629B2

Reaction notes

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