N-bromobutanimide → HCID 9835913, compound

HRID 1934785Notes

Reaction equation

HRID 1934785 reaction equation
[C:1]([N:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)#[N:2].[Br:18]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[C:1]([N:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[CH:6]([Br:18])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)#[N:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1116033810,11-Dihydro-5H-dibenzo[b,f]azepine-5-carbonitrile

Product 1

HCID 9835913HCID 9835913, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
2.5 °C

Procedure

6.60 g (0.030 mols) of 5-cyano-10,11-dihydro-5H-dibenz[b,f]-azepine (I) are stirred at 50° C. with 50 ml of CCl4. The fluid suspension is added under stirring with 5.6 g (0.0315 mols) of N-bromosuccinimide of purity above 98%, then with 0.37 g (0.0015 mols) of dibenzoylperoxide. Temperature is raised to mild reflux and the mixture is stirred for a further 55 minutes controlling the formed foam, then cooled and solvent is evaporated off. The residue is suspended in toluene (15 ml) at 80° C. for 20 minutes, filtered, the solution is cooled at 0-5° C. for 1 hour, to obtain 8.2 g (83%) of 5-cyano-10-bromo-10,11-dihydro-5H-dibenz[b,f]azepine (II), m.p. 132-9 (with decomposition).

Workup

  1. additionThe fluid suspension is added
  2. temperatureTemperature is raised
  3. temperatureto mild reflux
  4. temperaturecooled
  5. customsolvent is evaporated off
  6. waitThe residue is suspended in toluene (15 ml) at 80° C. for 20 minutes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-fbc9f8dfb17f42e088c6f9aefe52dea6
Source dataset
uspto-grants-2002_05
Patent number
US06384217B1

Reaction notes

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