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

HRID 1762710Notes

Reaction equation

HRID 1762710 reaction equation
[N:1]#[C:2]Br.[CH:4]1[C:14]2[C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][NH:10][CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1>C(Cl)(Cl)Cl>[CH:4]1[C:14]2[C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][N:10]([C:2]#[N:1])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 811835H-Dibenz(c,e)azepine, 6,7-dihydro-

Product 1

HCID 198338865,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1.91 g of cyanogen bromide in 20 ml of chloroform is added dropwise at 5°-10° C. within 25 minutes to a solution, cooled to 5° C., of 7 g of 6,7-dihydro-5H-dibenz[c,e]azepine in 50 ml of chloroform. The reaction mixture is stirred for a further 1 hour and then a small amount of the hydrobromide salt of the still unreacted azepine is filtered off. The filtrate is washed three times with water, dried over anhydrous sodium sulphate and evaporated. There is obtained solid 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile, m.p. 123°-126° C.

Workup

  1. filtrationa small amount of the hydrobromide salt of the still unreacted azepine is filtered off
  2. washThe filtrate is washed three times with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-5679784e42884e2e8dcffd5a0a8d5d0f
Source dataset
uspto-grants-1989_05
Patent number
US04833245

Reaction notes

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