Sodium Bisulfate → 10,11-Dihydro-10-oxo-5H-dibenz(b,f)azepine-5-carbonitrile

HRID 1934793Notes

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].[O-]Cl.[Na+].[OH:21]S([O-])(=O)=O.[Na+]>C(Cl)Cl>[C:1]([N:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[C:6](=[O:21])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

20 g (85 mmols) of (I) are dissolved in 120 ml of CH2Cl2. The solution is cooled to 0° C. and added with 0.24 g of 2,2,6,6-tetramethylpiperidine nitroxide, then with 180 ml of 1.4M NaClO, adjusted to pH 8.3 with a NaHSO4 saturated solution. The mixture is left for 1 hour at 0° C., then warmed to 20° C. for 4 hours. The organic phase is separated and washed with 50 ml of water, dried with 2 g of Na2SO4 and solvent is evaporated off. The residue is taken up with 50 ml of acetone and kept at 0° C. for 2 hours. The mixture is filtered, washed with 50 ml of cold acetone, dried at 60° C. for 4 hours to obtain 17 g of 5-cyano-10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine (VII), m.p. 153-4° C., with 98.5% purity by HPLC (85% yield).

Workup

temperaturewarmed to 20° C. for 4 hours
customThe organic phase is separated
washwashed with 50 ml of water
dry with materialdried with 2 g of Na2SO4 and solvent
customis evaporated off
waitkept at 0° C. for 2 hours
filtrationThe mixture is filtered
washwashed with 50 ml of cold acetone
customdried at 60° C. for 4 hours

Sources & evidence

ORD record: ord-8d7a5fbf5166457587177d427a61d5b3
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384217B1

Reaction notes

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