HCID 12962152, compound → HCID 12962153, compound

HRID 1156283Notes

Reaction equation

HRID 1156283 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10](Cl)[C:4]=2[CH:3]=1.[C:18]([Cu])#[N:19]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]([C:18]#[N:19])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 12962152HCID 12962152, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 12962153HCID 12962153, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,11-Dichloro-6,11-dihydrodibenz[b,e]oxepin (7.7 g; 0.03 mole) of example 25-A is dissolved in dry toluene (120 ml) and placed under a positive dry nitrogen atmosphere. To this solution is added CuCN (5.2 g; 0.05 mole) in one portion and the reaction brought to reflux for 61/2 hours. The reaction mixture is filtered while hot (80° C.) and the salts washed with tolune. After removing the filtrate in vacuo the resulting solid is triturated with hexane and dried to yield 2-chloro-11-cyano-6,11-dihydrodibenz[b,e]oxepin, m.p. 113°-115° C.

Workup

  1. temperatureto reflux for 61/2 hours
  2. filtrationThe reaction mixture is filtered while hot (80° C.)
  3. washthe salts washed with tolune
  4. customAfter removing the filtrate in vacuo the resulting solid
  5. customis triturated with hexane
  6. customdried

Sources & evidence

ORD record
ord-209dec11a3184b1f8e41086c4d27132a
Source dataset
uspto-grants-1982_06
Patent number
US04335122

Reaction notes

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