Potassium Carbonate → N-(2,4-difluorophenyl)-N-(pyridin-3-ylmethyl)butanesulfonamide

HRID 2351980Notes

Reaction equation

HRID 2351980 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23]([S:27](Cl)(=[O:29])=[O:28])[CH2:24][CH2:25][CH3:26].C(=O)(O)[O-].[Na+].[OH-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[S:27]([CH2:23][CH2:24][CH2:25][CH3:26])(=[O:29])=[O:28]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 754301-Butanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 110961292,4-difluoro-N-(pyridin-3-ylmethyl)aniline

Product 1

HCID 14720307N-(2,4-difluorophenyl)-N-(pyridin-3-ylmethyl)butanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 4.4 g. portion of 3-(2,4-difluorophenylaminomethyl)pyridine was dissolved in 15 ml. of dichloromethane, and to it were added 4.1 g. of potassium carbonate and 4.7 g. of butanesulfonyl chloride. The mixture was stirred under gentle reflux for several days, and was then cooled and diluted with 20 ml. of aqueous sodium bicarbonate and 5 ml. of aqueous sodium hydroxide. Some additional dichloromethane was added, and the suspension was shaken and the organic layer separated. It was washed with aqueous sodium bicarbonate and dried over magnesium sulfate, and it was then evaporated to a smaller volume and was chromatographed on a silica gel column, eluting with dichloromethane. The chromatography was repeated twice to obtain 0.38 g. of the desired product.

Workup

  1. temperatureunder gentle reflux for several days
  2. temperaturewas then cooled
  3. additiondiluted with 20 ml
  4. stirringthe suspension was shaken
  5. customthe organic layer separated
  6. washIt was washed with aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate, and it
  8. customwas then evaporated to a smaller volume
  9. customwas chromatographed on a silica gel column
  10. washeluting with dichloromethane
  11. customto obtain 0.38 g

Sources & evidence

ORD record
ord-9d3472ff94bf4e0a83f430fb815d192a
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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