4-Nitrobenzyl chloride → 4-(4-Chlorobenzoyl)-1-(4-nitrobenzyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

HRID 2417456Notes

Reaction equation

HRID 2417456 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[NH:11][C:10](=[O:19])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[N+:24]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1)([O-:26])=[O:25].C(OCC)(=O)C>CN(C=O)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]([CH2:31][C:30]3[CH:33]=[CH:34][C:27]([N+:24]([O-:26])=[O:25])=[CH:28][CH:29]=3)[C:10](=[O:19])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 74824-Nitrobenzyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 226325544-(4-Chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

Product 1

HCID 226324694-(4-Chlorobenzoyl)-1-(4-nitrobenzyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

110 mg (0.37 mmol) of 4-(4-chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on was dissolved in 5 ml of DMF. 17 mg (0.44 mmol) of sodium hydride was added to the obtained solution, and they were stirred at room temperature for 30 minutes. 76 mg (0.44 mmol) of 4-nitrobenzyl chloride was added to the obtained mixture and they were stirred at 60° C. overnight. The reaction mixture was treated with ethyl acetate as the extracting solvent by an ordinary method to obtain the crude product. After the purification by the silica gel column chromatography, the title compound was obtained.

Workup

  1. stirringwere stirred at 60° C. overnight
  2. customto obtain the crude product
  3. customAfter the purification by the silica gel column chromatography

Sources & evidence

ORD record
ord-01905b1ade1a4255994994f9bea9683c
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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