Water → 5-(4-Methylaminophenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione

HRID 1852503Notes

Reaction equation

HRID 1852503 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]([N:23]([CH3:36])S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)=[CH:19][CH:18]=2)[C:4](=[O:37])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1.O>CN(C)C=O>[CH3:36][NH:23][C:20]1[CH:19]=[CH:18][C:17]([N:5]2[C:4](=[O:37])[CH2:3][C:2](=[O:1])[NH:8][C:7]3[C:9]4[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=4[CH:15]=[CH:16][C:6]2=3)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 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-nitrobenzenesulfonamide

Product 1

HCID 866893205-(4-Methylaminophenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione

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]-N-methyl-2-nitrobenzenesulfonamide (50 mg, 0.096 mmol) was dissolved in dry dimethylformamide (2 mL). To the solution were added potassium carbonate (40 mg, 0.29 mmol), and then thiophenol (12 μL, 0.12 mmol). The mixture was stirred overnight at room temperature. To the reaction mixture was added cold water. The mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give 5-(4-methylaminophenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione as a colorless amorphous form (32 mg, 0.095 mmol).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by evaporation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-13ee15beffda487e868dfc6a0330015f
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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