Water → 10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carbonitrile
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].[OH2:25]>>[C:8]([N:10]1[C:11]2[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=2[CH:13]([OH:25])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2)#[N:9]Participants
4
Conditions
- Temperature
- 87.5 °C
Procedure
190 ml of chlorobenzene, 25 g of (I) and 17 g of N,N-dibromohydantoin are loaded into a 500 ml pyrex round-bottom flask, under nitrogen, and irradiated from the outside with a 300 watt halogen lamp, keeping temperature between 70 and 75° C. for 3 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., filtered and dried at 60° C. for 4 hours, to obtain 16 g of (VI), m.p. 110-111° C., with good purity.
Workup
- customtemperature between 70 and 75° C.
- customfor 3 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.
- filtrationfiltered
- customdried at 60° C. for 4 hours
Sources & evidence
- ORD record
- ord-ac843ac792d04321aab6641c33b4bb39
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06384217B1
Reaction notes
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