Methyl iodide → N-[4-(2,4-Dioxo-1,2,3,4,8,9,10,11-octahydronaphtho[1,2-b][1,4]diazepine-5-yl)phenyl]-N-methyl-2-nitrobenzenesulfonamide

HRID 1852502Notes

Reaction equation

HRID 1852502 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[CH:15]=[CH:16][C:6]=2[N:5]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N+:33]([O-:35])=[O:34])(=[O:26])=[O:25])=[CH:19][CH:18]=2)[C:4](=[O:36])[CH2:3]1.CI.[C:39](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:1]=[C:2]1[NH:8][C:7]2[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[CH:15]=[CH:16][C:6]=2[N:5]([C:17]2[CH:18]=[CH:19][C:20]([N:23]([CH3:39])[S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N+:33]([O-:35])=[O:34])(=[O:26])=[O:25])=[CH:21][CH:22]=2)[C:4](=[O:36])[CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86689317N-[4-(2,4-Dioxo-1,2,3,4,8,9,10,11-octahydronaphtho[1,2-b][1,4]diazepine-5-yl)phenyl]-2-nitrobenzenesulfonamide

Product 1

HCID 86689319N-[4-(2,4-Dioxo-1,2,3,4,8,9,10,11-octahydronaphtho[1,2-b][1,4]diazepine-5-yl)phenyl]-N-methyl-2-nitrobenzenesulfonamideYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[4-(2,4-Dioxo-1,2,3,4,8,9,10,11-octahydronaphtho[1,2-b][1,4]diazepine-5-yl)phenyl]-2-nitrobenzenesulfonamide (150 mg, 0.3 mmol), methyl iodide (22 μL, 0.36 mmol), potassium carbonate (45 mg, 0.33 mmol), and dry dimethylformamide (3 mL) were mixed. The mixture was stirred at room temperature for 16 hours. The solvent was removed by evaporation under reduced pressure. To the residue was added water. The mixture was stirred at room temperature. Insoluble was obtained by filtration, washed with water, and air-dried overnight to give the titled compound as off-white crystal (112 mg, yield 73%).

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. additionTo the residue was added water
  3. stirringThe mixture was stirred at room temperature
  4. customInsoluble was obtained by filtration
  5. washwashed with water
  6. customair-dried overnight

Sources & evidence

ORD record
ord-2ee3667cb31e41a2a30442a299ad6f8e
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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