Sodium Iodide → (3RS)-1,3-dihydro-5-phenyl-3-phthalimido-2H-1,4-benzodiazepine-2-one

HRID 1073704Notes

Reaction equation

HRID 1073704 reaction equation
C(O[CH:5]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=2[NH:7][C:6]1=[O:22])(=O)C.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[K].[I-].[Na+].CN(C)C=O>O>[C:12]1([C:10]2[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[NH:7][C:6](=[O:22])[CH:5]([N:27]3[C:26](=[O:28])[C:25]4=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]4[C:23]3=[O:33])[N:11]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 661451Stk563490HCID 24194345Phthalimide potassium salt

Product 1

HCID 14800302(3RS)-1,3-dihydro-5-phenyl-3-phthalimido-2H-1,4-benzodiazepine-2-oneYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (3RS)-1,3-dihydro-3-acetoxy-5-phenyl-2H-1,4-benzodiazepine-2-one (11.75 g), potassium phthalimide (11.1 g), sodium iodide (60 g) and N,N-dimethylformamide (80 ml) was stirred for 45 minutes at 90° to 95° C. The reaction mixture was poured into a cold water (1 l). The precipitates were collected by filtration, washed with water and recrystallized from ethanol to give (3RS)-1,3-dihydro-5-phenyl-3-phthalimido-2H-1,4-benzodiazepine-2-one (8.32 g).

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with water
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7c13e8d98a4e40afa67d7cb78a17c7c4
Source dataset
uspto-grants-1990_11
Patent number
US04970207

Reaction notes

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