Sodium Azide → 3-Azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 1456631

Reaction equation

HRID 1456631 reaction equation
I[CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C)C=O>[N:14]([CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13])=[N+:15]=[N-:16]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 110334773-iodo-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

Product 1

HCID 109325203-Azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 36.7 g (128 mmol) of 3-Iodo-2,3,4,5-tetrahydro-1H-[1]-benzazapin-2-one in 200 mL of dimethylformamide was added 9.97 g (153 mmol) of sodium azide. After 3 h, the mixture was poured into 800 mL of ice water and the precipitate collected on a filter. After washing the solid successively with water, 3% aqueous sodium bisulfite, and water, the product was dried under vacuum to give 21.5 g (83%) of a tan powder. 1H NMR (300 MHz, CDCl3) d 8.91 (1H, bs), 7.4-7.0 (4H, m), 3.89 (1H, t, J=9 Hz), 2.97 (1H, m), 2.73 (1H, m), 2.52 (1H, m), 2.32 (1H, m).

Workup

  1. customthe precipitate collected on a filter
  2. washAfter washing the solid successively with water, 3% aqueous sodium bisulfite, and water
  3. customthe product was dried under vacuum

Sources & evidence

ORD record
ord-75cc96b3e23e427691baa875e6e5676f
Source dataset
uspto-grants-1998_12
Patent number
US05843941

Linked notes

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