Sodium Cyanide → 9-Cyanomethyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

HRID 894191Notes

Reaction equation

HRID 894191 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][O:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[C:8](=[O:17])[C:7]=2[CH:18]=1.[C-:19]#[N:20].[Na+]>CN(C)C=O.O>[C:19]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][O:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[C:8](=[O:17])[C:7]=2[CH:18]=1)#[N:20]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 211627239-Bromomethyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

Product 1

HCID 211627269-Cyanomethyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolve 6.4 gm of the bromomethyl compound of Step C in 75 cc of dimethylformamide and add 2.95 gm of sodium cyanide. Stir the mixture at room temperature for 1.5 hours. Dilute with 600 cc of water and extract three times with ether. Wash the combined organics with water, dry and strip to a solid residue. Triturate in hexane and recover the solid by filtration.

Workup

  1. extractionextract three times with ether
  2. washWash the combined organics with water
  3. customdry
  4. customTriturate in hexane
  5. customrecover the solid
  6. filtrationby filtration

Sources & evidence

ORD record
ord-f2ceabd323ad4e6ab2fdf14891ece8fc
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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