Potassium Chloride → (+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbonitrile

HRID 25059

Reaction equation

HRID 25059 reaction equation
[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][NH:3]1.[CH3:25][N:26](C)C=O.[Cl-].[K+].N#CBr>O>[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25]#[N:26]

Participants

6

Reactant 4

HCID 4873Potassium ChlorideHCID 6228DimethylformamideHCID 10476Cyanogen BromideHCID 103364221-(4-Nitrophenyl)-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine

Product 1

HCID 12137416(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.25 g (10 mmol) of (±)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine, 20 ml of dimethylformamide, 2.76 g (20 mmol) of potassium chloride and 1.80 g (17 mmol) of cyanogen bromide was stirred at room temperature for 20 h. After pouring into water, the precipitated crystals were filtered off, and washed with water to yield 3.34 g (95%) of the title compound, Mp.: 172-176° C.

Workup

  1. filtrationthe precipitated crystals were filtered off
  2. washwashed with water

Sources & evidence

ORD record
ord-fc559d231c654a62a357da91edbcf1d0
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Linked notes

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