Chloroform → 9-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin

HRID 894173Notes

Reaction equation

HRID 894173 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][O:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[O:16])[C:6]=2[CH:17]=1.[CH3:18][N:19](C)C=O.C(Cl)(Cl)Cl.[C-]#N.[Na+]>O>[O:16]=[C:7]1[C:6]2[CH:17]=[C:2]([C:18]#[N:19])[CH:3]=[CH:4][C:5]=2[CH2:11][O:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]1=2

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 129291399-Bromo-6,11-dihydro-11-oxodibenz[b,e]oxepin

Product 1

HCID 129291409-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reflux a mixture of 9.13 gm. (0.0316 mole) of 9-bromo-6,11-dihydro-11-oxodibenz[b,e]oxepin, 6.03 gm. (0.0673 mole) of cuprous cyanide and 32 ml. of dimethylformamide for 4 hours with vigorous stirring. Cool the reaction mixture and shake with a mixture of 45 ml. of chloroform, 32 ml. of saturated sodium cyanide solution and 32 ml. of water until all solids have dissolved. Separate the organic layer and wash with aqueous sodium cyanide solution and water. Dry over anhydrous magnesium dulfate. Remove the solvent to obtain the title product (yield 7.43 gm., m.p. 116°-127° C.).

Workup

  1. temperatureReflux
  2. additiona mixture of 9.13 gm
  3. temperatureCool the reaction mixture and shake
  4. additionwith a mixture of 45 ml
  5. customSeparate the organic layer
  6. washwash with aqueous sodium cyanide solution and water
  7. dry with materialDry over anhydrous magnesium dulfate
  8. customRemove the solvent

Sources & evidence

ORD record
ord-099d9a07dc03407cbc461231ee2b2da5
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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