Dimethylformamide → HCID 178421800, compound

HRID 25082

Reaction equation

HRID 25082 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][N:3]1[C:25]#[N:26].CN(C)C=O.[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+]>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:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)=[N:4][N:3]1[C:25]1[NH:34][N:33]=[N:32][N:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12137416(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbonitrile

Product 1

HCID 178421800HCID 178421800, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 0.60 g (1.70 mmol) of the starting material XXIII, 3 ml of dimethylformamide, 0.12 g (1.87 mmol) of sodium azide and 0.10 g (1.87 mmol) of ammonium chloride was stirred at 140° C. for 30 min. The cooled reaction mixture was diluted with water and the precipitated crystals were filtered off. The so obtained product was purified by column chromatography using silica gel (MN Kieselgel 60) as adsorbent and a mixture of chloroform-methanol (99:1) as eluent to yield 0.68 g (54%) of the title compound; Mp.: 263-264° C.

Workup

  1. customThe cooled reaction mixture
  2. filtrationthe precipitated crystals were filtered off
  3. customThe so obtained product
  4. customwas purified by column chromatography
  5. additiona mixture of chloroform-methanol (99:1) as eluent

Sources & evidence

ORD record
ord-2ca105df26b446e984445b4e84d6a6c2
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Linked notes

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