Methanol → 9Chloro-6,11-dihydro-5H-dibenz[b,e]azepine
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=O)[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=O)[C:6]=2[CH:18]=1.[B].CSC.CO>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][C:6]=2[CH:18]=1Participants
Procedure
To a mixture of 7.28 g of 9-chloro-5H-dibenz[b,e]azepin-6,11-dione in 25 ml of tetrahydrofuran under argon is added 8.5 ml of 10 molar boron-dimethylsulfide in tetrahydrofuran. The mixture is stirred 18 hours at room temperature, 30 ml of tetrahydrofuran added and the mixture refluxed for 3 hours (solids dissolved). The solution is cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum. To the residue is added 100 ml of 2N NaOH. The mixture is refluxed overnight and filtered. The solid is extracted with dichloromethane and the extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed to give 4.2 g of solid which is triturated with ethyl acetate-hexane (1:2) to give crystals, m.p. 137° C. to 141° C.
Workup
- temperaturethe mixture refluxed for 3 hours
- dissolution(solids dissolved)
- temperatureThe solution is cooled to room temperature
- customThe volatiles are removed under vacuum
- additionTo the residue is added 100 ml of 2N NaOH
- temperatureThe mixture is refluxed overnight
- filtrationfiltered
- extractionThe solid is extracted with dichloromethane
- washthe extract is washed with 2N citric acid, water
- dry with materialdried (Na2SO4)
- customThe solvent is removed
Sources & evidence
- ORD record
- ord-86e7249d952d4430a40688e3ea760458
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05869483
Reaction notes
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