Ethyl Acetate → 1-(4-Bromobenzyl)-4-(4-chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

HRID 2417455Notes

Reaction equation

HRID 2417455 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+].[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1.C(OCC)(=O)C>CN(C=O)C>[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:11]2[C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[CH2:14][N:8]([C:6](=[O:7])[C:5]3[CH:20]=[CH:21][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:9][C:10]2=[O:19])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 226325544-(4-Chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

Product 1

HCID 226323321-(4-Bromobenzyl)-4-(4-chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 mg (0.067 mmol) of 4-(4-chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on was dissolved in 5 ml of DMF. 3 mg (0.8 mmol) of sodium hydride was added to the obtained solution, and they were stirred at room temperature for 30 minutes. 20 mg (0.08 mmol) of 4-bromobenzyl bromide 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-ed052688065246c3acf63ef993e55515
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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