11-Chloro-6,11-dihydrodibenz[b,e]oxepin → HCID 12962149, compound

HRID 1156276Notes

Reaction equation

HRID 1156276 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[C:17]([Cu])#[N:18]>C1C=CC=CC=1>[C:17]([CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2)#[N:18]

Participants

4

Reactant 2

HCID 1296214811-Chloro-6,11-dihydrodibenz[b,e]oxepinHCID 178418546HCID 178418546, compound

Product 1

HCID 12962149HCID 12962149, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

11-Chloro-6,11-dihydrodibenz[b,e]oxepin (32.69 g; 0.14 mole) is dissolved in dry benzene (300 ml) and placed under a dry nitrogen atmosphere. To this solution is added in one portion, CuCN (32.04 g; 0.35 mole). The reaction is heated to reflux for 31/2 hours and filtered while hot. After washing the salts with benzene, the filtrate is removed in vacuo to give a solid. This solid is triturated several times with isopropyl ether and finally hexane to give a solid (92%) of 11-cyano-6,11-dihydrodibenz[b,e]oxepin m.p. 65°-66.5° C.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux for 31/2 hours
  3. filtrationfiltered while hot
  4. washAfter washing the salts with benzene
  5. customthe filtrate is removed in vacuo
  6. customto give a solid
  7. customThis solid is triturated several times with isopropyl ether and finally hexane

Sources & evidence

ORD record
ord-561e7c14108a4d719f96242573b9a7d0
Source dataset
uspto-grants-1982_06
Patent number
US04335122

Reaction notes

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