Methyl iodide → 1-methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one
Reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH2:4][CH2:3][C:2]1=[O:12].[H-].[Na+].[CH3:15]I>CN(C=O)C>[CH3:15][N:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH2:4][CH2:3][C:2]1=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To a solution of 2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one (2.0 g, 12.3 mmol) in DMF (30 ml), at −10° C., was added sodium hydride (0.54 g, 60% dispersion, 13.6 mmol). The mixture was stirred at −10° C. for 15 min, then methyl iodide (0.77 ml, 12.3 mmol) was added. The mixture was stirred at −100° C. for a further 1 h and then concentrated in vacuo. The residue was taken up in EtOAc and washed with brine (3 times), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc) to give a white solid; yield 1.70 g (78%).
Workup
- stirringThe mixture was stirred at −100° C. for a further 1 h
- concentrationconcentrated in vacuo
- washwashed with brine (3 times)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography on silica (eluant EtOAc)
- customto give a white solid
Sources & evidence
- ORD record
- ord-1dda44b9a045499aa85555de3768b7fb
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07176195B2
Reaction notes
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