Benzoyl Peroxide → 10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carbonitrile

HRID 1934790Notes

Reaction equation

ClC1C=CC=CC=1.[C:8]([N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][CH2:13][C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]1=2)#[N:9].BrN1C(=[O:31])CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>O>[C:8]([N:10]1[C:11]2[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=2[CH:13]([OH:31])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2)#[N:9]

Participants

Conditions

Temperature: 87.5 °C

Procedure

190 ml of chlorobenzene and 25 g of (I) are loaded into a 500 ml pyrex round-bottom flask, under nitrogen. Afterwards, 21.2 g of N-bromosuccinimide and 2.2 g of dibenzoylperoxide are added and the mixture is heated to 85-90° C., keeping this temperature for 1.5 hours. 150 ml of water and 5 g of PEG 6000 are added, heating to 85°-90° C. for 2 hours. After decanting at 60° C., water is removed and the organic phase is washed with further water (2×100 ml). Chlorobenzene is evaporated off under vacuum at 5 mm/Hg and the residue is taken up with 50 ml of ethyl acetate. The mixture is cooled to 0° C. for 2 hours, filtered and dried at 60° C. for 4 hours, to obtain 14 g of (VI), m.p. 111-112° C., with good purity.

Workup

customfor 1.5 hours
temperatureheating to 85°-90° C. for 2 hours
customAfter decanting at 60° C.
customwater is removed
washthe organic phase is washed with further water (2×100 ml)
customChlorobenzene is evaporated off under vacuum at 5 mm/Hg
temperatureThe mixture is cooled to 0° C. for 2 hours
filtrationfiltered
customdried at 60° C. for 4 hours

Sources & evidence

ORD record: ord-0e85edefc5be4c85824275ffef2c5e78
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384217B1

Reaction notes

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