Sodium Iodide → 7-Iodomethyl-6,7-dihydro-dibenzo[c,e]azepin-5-one
Reaction equation
[O:1]=[C:2]1[NH:8][CH:7]([CH2:9]OS(C)(=O)=O)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[C:4]2[CH:19]=[CH:20][CH:21]=[CH:22][C:3]1=2.[Na+].[I-:24]>CC(C)=O>[I:24][CH2:9][CH:7]1[NH:8][C:2](=[O:1])[C:3]2[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=2[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]1=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of methanesulfonic acid 7-oxo-6,7-dihydro-5H-dibenzo[c,e]azepin-5-ylmethyl ester in acetone (5 mL) is added NaI and the mixture is stirred at 50° C. for 18 h. The solvent is removed under reduced pressure and EtOAc is added. The solution is washed sequentially with sodium bisulfite solution, water and brine and is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 0-100% EtOAc/hexane as eluent to give the title compound as a yellow solid.
Workup
- customThe solvent is removed under reduced pressure and EtOAc
- additionis added
- washThe solution is washed sequentially with sodium bisulfite solution, water and brine
- dry with materialis dried over magnesium sulfate
- customThe solvent is removed under reduced pressure
- customthe residue purified by flash chromatography
Sources & evidence
- ORD record
- ord-da824801aaa74aaca49c1fab59bbd607
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084448B2
Reaction notes
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