Reacción #63450

Ecuación de reacción

sodium hydroxide

cyanamide

benzene

2,2'-bis(bromomethyl)-biphenyl

→

5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling the reaction mixture
2. 2
   Otrothis is transferred to a separating funnel
3. 3
   ExtracciónThe aqueous phase is back-extracted twice with methylene chloride
4. 4
   LavadoThe combined extracts are subsequently washed with water
5. 5
   Secadodried over anhydrous sodium sulphate
6. 6
   Otroevaporated
7. 7
   Temperaturathe solution is heated
8. 8
   Temperaturato reflux temperature
9. 9
   Filtraciónfiltered
10. 10
    workup.ADDITIONtreated at about 50° C. with 200 ml of tert.-butyl methyl ether
11. 11
    OtroFinally, the crystals which are precipitated by ice-
12. 12
    Temperaturacooling
13. 13
    Filtraciónare filtered off under suction
14. 14
    Otrodried

Procedimiento

180 ml of 50% sodium hydroxide solution are treated at about 60° C. in sequence with 7.7 g of cyanamide, 1.3 g of tricaprylmethylammonium chloride, 360 ml of benzene and 62 g of 2,2'-bis(bromomethyl)-biphenyl, and the mixture is stirred at 60°-70° C. for 6 hours. After cooling the reaction mixture this is transferred to a separating funnel and shaken with 50 ml of methylene chloride, whereby the separated product is taken up in the methylene chloride phase. The aqueous phase is back-extracted twice with methylene chloride. The combined extracts are subsequently washed with water, dried over anhydrous sodium sulphate and evaporated, and the residue is taken up in 100 ml of toluene and the solution is heated to reflux temperature, filtered and treated at about 50° C. with 200 ml of tert.-butyl methyl ether. Finally, the crystals which are precipitated by ice-cooling are filtered off under suction and dried. In this manner there is obtained pure 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile, m.p. 121°-124° C.

Fuente