Sodium Cyanide → 3-Cyanomethyl-10,11-dihydro-11-oxodibenzo[b,f]thiepin

HRID 1075019Notes

Reaction equation

HRID 1075019 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12](=[O:13])[CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[S:8][C:7]=2[CH:18]=1.[C-:19]#[N:20].[Na+]>CN(C)C=O>[C:19]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12](=[O:13])[CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[S:8][C:7]=2[CH:18]=1)#[N:20]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 202702683-Bromomethyl-10,11-dihydro-11-oxodibenzo[b,f]thiepin

Product 1

HCID 202702303-Cyanomethyl-10,11-dihydro-11-oxodibenzo[b,f]thiepin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 6.4 gm. of the bromide of Step 2 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. dissolutionDissolve 6.4 gm
  2. additionDilute with 600 cc
  3. extractionof water and extract three times with ether
  4. washWash the combined organics with water
  5. customdry
  6. customTriturate in hexane
  7. customrecover the solid
  8. filtrationby filtration

Sources & evidence

ORD record
ord-acde7dea38374252aa002e970daa77bb
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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