Sodium Iodide → (+/-)-7-(4,5-Dihydro-oxazol-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

HRID 25071Notes

Reaction equation

HRID 25071 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([N:7]1[CH:13]([CH3:14])[CH2:12][C:11]2[CH:15]=[C:16]3[O:21][CH2:20][O:19][C:17]3=[CH:18][C:10]=2[C:9]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[N:8]1)=[O:6].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].CN(C)C=O>O>[O:6]1[CH2:2][CH2:3][N:4]=[C:5]1[N:7]1[CH:13]([CH3:14])[CH2:12][C:11]2[CH:15]=[C:16]3[O:21][CH2:20][O:19][C:17]3=[CH:18][C:10]=2[C:9]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[N:8]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12137418(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carboxylic acid (2-chloroethyl)-amide

Product 1

HCID 22565447(+/-)-7-(4,5-Dihydro-oxazol-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineYield 76.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 1.43 g (3.32 mmol) of the starting material XXV, 1.38 g (9.98 mmol) of anhydrous potassium carbonate, 0.24 g (1.60 mmol) of sodium iodide and 24 ml of dimethylformamide was stirred at 100-110° C. for 4 h. Then the mixture was diluted with water and the precipitated crude product was recrystallized from ethanol to yield 1.00 g (76%) of the title compound; Mp.: 194-196° C.

Workup

  1. customthe precipitated crude product
  2. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-bbcd50fcc25f4f5c91fcd5d73bcc8b28
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Reaction notes

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