5H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro- → 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile
Reaction equation
[Sn](Cl)(Cl)(Cl)Cl.Cl[CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2.C[Si]([C:26]#[N:27])(C)C>C(Cl)Cl.O>[C:26]([CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2)#[N:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
6.0 g (23.0 mmol) of tin tetrachloride are slowly added to a solution of 21.1 g (92.3 mmol) of 5-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene [V. Mychajlyszyn et al, Coll. Czech. Chem. Comm. 24, 3955 (1959)] and 11.3 g (114 mmol) of trimethylsilylcyanide in 150 ml of methylene chloride. The reaction mixture is stirred at room temperature for 10 hours and then diluted with 150 ml of methylene chloride, and 200 ml of water are added. The organic phase is separated off, washed with dilute sodium bicarbonate solution, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Crystallization of the residue from toluene gives 18.0 g (88.9%) of 5-cyano-10,11-dihydro-5H-dibenzo[a,d]-cycloheptene, melting point 89°-90° C. (compound (104), Table 1).
Workup
- additionare added
- customThe organic phase is separated off
- washwashed with dilute sodium bicarbonate solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated on a vacuum rotary evaporator
- customCrystallization of the residue from toluene
Sources & evidence
- ORD record
- ord-c7af6449320b467ca13f1ccdb638a4d1
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05844024
Reaction notes
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