Potassium Carbonate → N-(4-fluorophenyl)-N-(pyridin-3-ylmethyl) methanesulfonamide

HRID 2352002Notes

Reaction equation

HRID 2352002 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(=O)(O)[O-].[Na+].[OH-].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[S:23]([CH3:22])(=[O:25])=[O:24])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 645683N-(4-Fluorophenyl)-3-pyridinemethanamine

Product 1

HCID 14720344N-(4-fluorophenyl)-N-(pyridin-3-ylmethyl) methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2.3 g. portion of 3-(4-fluorophenylaminomethyl)pyridine was dissolved in 15 ml. of dichloromethane, and 2.1 g. of potassium carbonate and 1.2 ml. of methanesulfonyl chloride were added. The mixture was stirred under reflux for 2 days, and was then cooled and diluted with 20 ml. of aqueous sodium bicarbonate and 5 ml. of 2N sodium hydroxide. The organic phase was washed again with aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated under vacuum. The residue was triturated with hot diethyl ether, and the solids were filtered and dried to obtain 2.6 g. of the desired product, m.p. 112°-113°.

Workup

  1. temperatureunder reflux for 2 days
  2. temperaturewas then cooled
  3. additiondiluted with 20 ml
  4. washThe organic phase was washed again with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue was triturated with hot diethyl ether
  8. filtrationthe solids were filtered
  9. customdried
  10. customto obtain 2.6 g

Sources & evidence

ORD record
ord-d4193da75f3e4531b70060386d2a20f3
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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