Water → 5-Chloro-N-(4-methoxybenzyl)-N-methylpyridine-2-sulfonamide

HRID 909658Notes

Reaction equation

HRID 909658 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[N:6][CH:7]=1.[H-].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=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]([CH2:21][C:20]2[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[CH3:12])(=[O:10])=[O:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 666831865-chloro-N-methylpyridine-2-sulfonamide

Product 1

HCID 666813895-Chloro-N-(4-methoxybenzyl)-N-methylpyridine-2-sulfonamideYield 58.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Chloro-N-methylpyridine-2-sulfonamide (889 mg, 4.30 mmol) synthesized in Example (121a) was dissolved in N,N-dimethylformamide (15 mL), and sodium hydride (172 mg, 4.30 mmol) was added. After ice cooling, p-methoxybenzyl chloride (0.70 mL, 5.16 mmol) was added, and the temperature was raised to room temperature, followed by stirring for 3 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=0%-20%) to afford the desired compound (817 mg, yield 58%) as a colorless oil.

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=0%-20%)

Sources & evidence

ORD record
ord-54197a2e40ed427a98cebe4041812e3c
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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