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

HRID 1903383Notes

Reaction equation

HRID 1903383 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:16][N:17](C)C(=O)C.N#CCl>ClCCCl>[C:16]([N:6]1[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH:9]=[CH:10][C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)#[N:17]

Participants

5

Reactant 3

HCID 9212Dibenz(b,f)azepineHCID 10477Cyanogen Chloride2×HCID 31374Dimethylacetamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

By a procedure analogous to that described in Example 1, 97.0 g of 5H-dibenz[b,f]azepine are suspended in 320 ml of 1,2-dichloroethane, and 2 ml of N,N-dimethylacetamide are added. The temperature is raised to 60°, and 50 g of cyanogen chloride are introduced in the course of 2 hours, the reflux condenser being cooled to -17° in order to avoid loss of cyanogen chloride. The mixture is kept at 60° for 16 hours; a descending condenser is then fitted, and at normal pressure 200 ml of a mixture of cyanogen chloride and 1,2-dichloroethane are distilled off into a cooled receiver. During distillation, the 1,2-dichloroethane passing over is continuously replaced by fresh solvent in order to remove residual cyanogen chloride. The contents of the flask are cooled to room temperature; 200 ml of water are added, and the mixture is rendered permanently alkaline by the addition of 30% sodium hydroxide solution. Further processing, analogous to that in Example 2, yields 96.3 g of 5-cyano-5H-dibenz[b,f]azepine, which, according to the IR spectrum, is identical to authentic material; m.p. 108°-109°. A further 4 g of final product can be obtained from the mother liquor, and the total yield is 100.3 g (92% of theory).

Workup

  1. temperatureThe temperature is raised to 60°
  2. temperaturethe reflux condenser being cooled to -17° in order
  3. customa descending condenser is then fitted
  4. distillationat normal pressure 200 ml of a mixture of cyanogen chloride and 1,2-dichloroethane are distilled off into a cooled receiver
  5. distillationDuring distillation
  6. customto remove residual cyanogen chloride
  7. addition200 ml of water are added
  8. additionthe mixture is rendered permanently alkaline by the addition of 30% sodium hydroxide solution

Sources & evidence

ORD record
ord-0b14bd21a6aa4c4bb65a6a3048a8fc13
Source dataset
uspto-grants-1984_03
Patent number
US04436660

Reaction notes

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