2-Chloroethyl isocyanate → (+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carboxylic acid (2-chloroethyl)-amide

HRID 25061

Reaction equation

HRID 25061 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.[Cl:25][CH2:26][CH2:27][N:28]=[C:29]=[O:30]>ClCCl>[Cl:25][CH2:26][CH2:27][NH:28][C:29]([N:3]1[CH:2]([CH3:1])[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]1)=[O:30]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 103364221-(4-Nitrophenyl)-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine

Product 1

HCID 12137418(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carboxylic acid (2-chloroethyl)-amideYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g (3.07 mmol) of (±)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine, 25 ml of dry dichloromethane and 0.62 g (5.88 mmol of 2-chloroethyl isocyanate was stirred at room temperature for 24 h, then concentrated. The residue was purified by refluxing in ethanol to yield 1.25 g (94%) of the title compound, Mp.: 222-223° C.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified
  3. temperatureby refluxing in ethanol

Sources & evidence

ORD record
ord-2801449e76a54039a62ffd7aa20d7690
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Linked notes

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