Water → 5-Chloro-N,N-bis(4-methoxybenzyl)pyridine-2-sulfonamide

HRID 1964712Notes

Reaction equation

HRID 1964712 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[N:6][CH:7]=1.[H-].[Na+].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1.O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 666826565-Chloro-N-(4-methoxybenzyl)pyridine-2-sulfonamide

Product 1

HCID 666833875-Chloro-N,N-bis(4-methoxybenzyl)pyridine-2-sulfonamideYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Chloro-N-(4-methoxybenzyl)pyridine-2-sulfonamide (983 mg, 3.14 mmol) synthesized in Example (120a) was dissolved in N,N-dimethylformamide (5 mL), and sodium hydride (132 mg, 3.30 mmol) was added. After ice cooling, p-methoxybenzyl chloride (1.02 mL, 3.37 mmol) was added, and the temperature was raised to room temperature, followed by stirring for 2 hours. Water (20 mL) was added to the reaction solution, and extraction was carried out twice with ethyl acetate (20 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-100%) to afford the desired compound (1.14 g, yield 84%) as a white solid.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialsubsequently dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified
  5. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-100%)

Sources & evidence

ORD record
ord-d034b8c4ca2d46ab8edd00e06ec22d9b
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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