Sodium Azide → HCID 21801972, compound

HRID 1647829Notes

Reaction equation

HRID 1647829 reaction equation
Cl[CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]1=[O:19].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O.O>[N:20]([CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]1=[O:19])=[N+:21]=[N-:22]

Participants

5

Reactant 2

HCID 33557Sodium Azide2×HCID 19920996HCID 19920996, compound

Product 1

HCID 21801972HCID 21801972, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 5.0 g (0.0184 mole) of 3-chloro-1-phenyl-2,3,4,5-tetrahydro-1-benzoazepin-2(1H)-one and 1.8 g (0.0277 mole) of sodium azide suspended in 50 ml of dimethylformamide was stirred at a bath temperature of 80° C. overnight. Next, to the mixture was added 1.0 g (0.0154 mole) of sodium azide, and the mixture was stirred for 8 hours. The reaction mixture was diluted with water and then extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried, and the solvent was removed under reduced pressure to obtain a residue. The residue was recrystallized from ethyl acetate to obtain 3.58 g of the title compound as colorless crystals.

Workup

  1. stirringthe mixture was stirred for 8 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. customto obtain a residue
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-554212ff369f410f8603dc480ade50b9
Source dataset
uspto-grants-1995_07
Patent number
US05434148

Reaction notes

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