HCID 12962150, compound → HCID 12962151, compound

HRID 1156281Notes

Reaction equation

HRID 1156281 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][C:15]([O:17][CH3:18])=[CH:16][C:3]1=2.[C:19]([Cu])#[N:20]>C1C=CC=CC=1.CCCCCC>[C:19]([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][C:15]([O:17][CH3:18])=[CH:16][C:3]1=2)#[N:20]

Participants

5

Reactant 2

HCID 12962150HCID 12962150, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 12962151HCID 12962151, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8058HexaneSolvent

Procedure

11-Chloro-2-methoxy-6,11-dihydrodibenz[b,e]oxepin (10.1 g; 0.038 mole) of Example 24A is dissolved in dry benzene (170 ml) and placed under a dry nitrogen atmosphere. To this solution is added in one portion, CuCN (8.5 g; 0.095 mole). The reaction is brought to reflux (twenty minutes), filtered while hot and the salts are washed with benzene. Removal of the solvent in vacuo yields an oil. The oil is dissolved in a minimal amount of benzene and hexane is added with cooling. The resulting solid is filtered and recrystallized from ethanol to give a solid of 11-cyano-2-methoxy-6,11-dihydrodibenz[b,e]oxepin, m.p. 120°-122° C.

Workup

  1. temperatureto reflux (twenty minutes)
  2. filtrationfiltered while hot and the salts
  3. washare washed with benzene
  4. customRemoval of the solvent in vacuo
  5. customyields an oil
  6. additionis added
  7. temperaturewith cooling
  8. filtrationThe resulting solid is filtered
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-bfa2efbab2ef46849bde28977063d3f3
Source dataset
uspto-grants-1982_06
Patent number
US04335122

Reaction notes

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