Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:22])[CH2:10][N:9]=1.[CH2:23]1[O:25][CH2:24]1.[OH-].[NH4+]>C(Cl)CCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]12[O:25][CH2:24][CH2:23][N:9]1[CH2:10][C:11](=[O:22])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=12Participants
Procedure
A solution of 5.2 g (0.02 M) of stannic chloride in 60 ml of dry ethylene dichloride under nitrogen was treated with 2.9 g (0.0091 M) of 5-(2-chlorophenyl)-1,3-dihydro-7-nitro-2H-1,4-benzodiazepin-2-one. The reaction was cooled in an ice bath, and 2.6 g (0.06 M) of ethylene oxide in 10 ml of ethylene dichloride was added with stirring over an 8 min period. After 18 hr at room temperature, the solution was made basic with concentrated ammonium hydroxide and filtered. The filtrates were washed with a saturated solution of brine, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was crystallized from a mixture of dichloromethane, methanol and petroleum ether to give the above named product as white rods, melting at 201°-203° .
Workup
- temperatureThe reaction was cooled in an ice bath
- waitAfter 18 hr at room temperature
- filtrationfiltered
- washThe filtrates were washed with a saturated solution of brine
- dry with materialdried over anhydrous sodium sulfate
- customevaporated to dryness
- customThe residue was crystallized from a mixture of dichloromethane, methanol and petroleum ether
- customto give the above named product as white rods, melting at 201°-203°
Sources & evidence
- ORD record
- ord-ebeb7e760c434744a6d05b75d2b8ca5d
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04017532
Linked notes
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