Dimethylformamide → 3-Azido-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one

HRID 1687634Notes

Reaction equation

HRID 1687634 reaction equation
I[CH:2]1[CH2:8][C:7]([CH3:10])([CH3:9])[C:6]2[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:5]=2[NH:4][C:3]1=[O:18].[N-:19]=[N+:20]=[N-:21].[Na+].CN(C=O)C>>[N:19]([CH:2]1[CH2:8][C:7]([CH3:10])([CH3:9])[C:6]2[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:5]=2[NH:4][C:3]1=[O:18])=[N+:20]=[N-:21]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 672643563-Iodo-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one

Product 1

HCID 866339913-Azido-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one

Procedure

3-Iodo-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one (5.367 g, 0.015 mol), Sodium azide (6.49 g, 0.1 mol), and DMF (100 mL, 2 mol) were stirred at rt for 2 h. The reaction mixture was diluted with H20 and the resulting beige ppt was filtered.

Workup

  1. additionThe reaction mixture was diluted with H20
  2. filtrationthe resulting beige ppt was filtered

Sources & evidence

ORD record
ord-8f7adc16f7244274895898e7c92241f0
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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