Allyl bromide → HCID 67858361, compound

HRID 2082441Notes

Reaction equation

HRID 2082441 reaction equation
[CH2:1]1[C:6]2[C:7]3[N:8]([CH:19]=[N:20][N:21]=3)[C:9]3[CH:17]=[CH:16][C:15](=[O:18])[CH2:14][C:10]=3[N:11]3[CH:12]=[CH:13][C:4]([C:5]=23)=[CH:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30]>CN(C)C=O>[CH2:30]([CH:14]1[C:10]2[N:11]3[CH:12]=[CH:13][C:4]4[C:5]3=[C:6]([CH2:1][CH2:2][CH:3]=4)[C:7]3[N:8]([CH:19]=[N:20][N:21]=3)[C:9]=2[CH:17]=[CH:16][C:15]1=[O:18])[CH:29]=[CH2:28]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 67858201HCID 67858201, compound

Product 1

HCID 67858361HCID 67858361, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,2,4]triazolo[4,3-d][1,4]benzodiazepin-8(7H)-one (2.5 g) was dissolved in dimethylformamide (50 ml). Potassium carbonate (0.5 g) was added followed by allyl bromide (2.2 g). The reaction mixture was stirred at 95° C. overnight, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by high performance liquid chromatography (2% methanol/dichloromethane) to yield 1.9 g (65.9%) of product. Recrystallization from methanol gave the analytical sample, mp 109°-110° C.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by high performance liquid chromatography (2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-2cba3b6ef4174b42ba7fad66aa54fd28
Source dataset
uspto-grants-1993_02
Patent number
US05189161

Reaction notes

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