Benzyl Bromide → HCID 19696183, compound

HRID 863483Notes

Reaction equation

HRID 863483 reaction equation
[Br:1][C:2]1[C:3]2[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][C:4]=2[C:5]2[NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH2:21]([O:18][CH:15]1[CH2:14][C:4]2[C:5]3[NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]=3[CH:11]=[C:2]([Br:1])[C:3]=2[CH2:17][CH2:16]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 19696251HCID 19696251, compound

Product 1

HCID 19696183HCID 19696183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 6-bromo-9-hydroxy-1,4,7,8,9,10-hexahydrobenzo[f]quinoxaline-2,3-dione (0.1 g, 0.32 mmol) and sodium hydride (16 mg, 0.4 mmol) in dimethylformamide (1 mL) was stirred at 0° C. for 30 min, and then treated with benzyl bromide (70 mg, 0.4 mmol). The reaction mixture was stirred for 48 h and warmed to room temperature during that time. The solvent was removed by rotoevaporation, the residue triturated in ethyl acetate, and the solid collected by filtration and dried. CI MS m/e (M+1) 402, 404. H-NMR (200 MH2, dmso): 1H, s, 12.05; 1H, s, 11.95; 5H, m, 7.4-7.2; 1H, s, 7.05; 2H, s, 5.4; 1H, s, 4.75; 1H, m, 3.9; +ring protons.

Workup

  1. stirringThe reaction mixture was stirred for 48 h
  2. temperaturewarmed to room temperature during that time
  3. customThe solvent was removed by rotoevaporation
  4. customthe residue triturated in ethyl acetate
  5. filtrationthe solid collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-bfa51e52f1ad46908128d10706dac0c4
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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