Dibenz(b,f)azepine → 5H-Dibenz(b,f)azepine-5-carbonitrile

HRID 1903384Notes

Reaction equation

HRID 1903384 reaction equation
[N:1]#[C:2]Cl.[CH:4]1[C:14]2[CH:13]=[CH:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:2]([N:9]1[C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[CH:12]=[CH:13][C:14]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]1=2)#[N:1]

Participants

5

Reactant 2

HCID 9212Dibenz(b,f)azepineHCID 10477Cyanogen Chloride

Product 1

HCID 6127595H-Dibenz(b,f)azepine-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

6 g of cyanogen chloride are introduced within 1 hour into a solution, heated to 80°, of 9.64 g of 5H-dibenz[b,f]azepine and 1 g of benzyltriethylammonium chloride in 40 ml of toluene. The reaction mixture is stirred for a further 5 hours at 80°; it is then cooled to room temperature and washed with 40 ml of 2 N sodium hydroxide solution; the organic phase is separated, and is then evaporated to dryness in vacuo to obtain 5-cyano-5H-dibenz[b,f]azepine, which is identical to the product obtainable according to Example 1; m.p. 107°-108°; yield 6.2 g (56.9% of theory).

Workup

  1. washwashed with 40 ml of 2 N sodium hydroxide solution
  2. customthe organic phase is separated
  3. customis then evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-2fa07f15de2444a09c8238b9eb0f226c
Source dataset
uspto-grants-1984_03
Patent number
US04436660

Reaction notes

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