Benzenesulfonamide → N-[({2-[4-(3,5-Dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethyl}amino)carbonyl]benzenesulfonamide

HRID 891088Notes

Reaction equation

HRID 891088 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:13][C:14]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:17]([CH3:25])[N:16]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH:34][C:35](=O)[O:36]C3C=CC=CC=3)=[CH:28][CH:27]=2)[N:15]=1>CN(C)C=O>[CH3:13][C:14]1[C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:17]([CH3:25])[N:16]([C:26]2[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][NH:34][C:35]([NH:10][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])=[O:36])=[CH:30][CH:31]=2)[N:15]=1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 24758Sodium hydrideHCID 22244550Phenyl 2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylcarbamate

Product 1

HCID 22244539N-[({2-[4-(3,5-Dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethyl}amino)carbonyl]benzenesulfonamideYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of benzenesulfonamide (40 mg, 0.26 mmol), sodium hydride (11 mg, 0.49 mmol) and N,N-dimethylformamide (2 mL) was added dropwise a solution of phenyl 2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylcarbamate (step 1, 100 mg, 0.24 mmol) in N,N-dimethylformamide (2 mL) at room temperature. After 2 h, the mixture was poured into ice-water and extracted with dichloromethane. The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by TLC with dichloromethane/methanol (10:1) to give 84 mg (73%) of the title compound as white solids: 1H-NMR (CDCl3) δ 7.89 (2H, d, J=8.2 Hz), 7.64-7.21 (12H, m), 6.33 (1H, br.s), 3.51-3.44 (2H, m), 2.84 (2H, t, J=6.8 Hz), 2.33 (3H, s), 2.24 (3H, s).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by TLC with dichloromethane/methanol (10:1)

Sources & evidence

ORD record
ord-111d411f7ae641cc94141e12f2c79305
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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