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

HRID 2351995Notes

Reaction equation

HRID 2351995 reaction equation
ClC.[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[NH:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([S:27](Cl)(=[O:29])=[O:28])[CH3:26].C(=O)(O)[O-].[Na+]>>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[N:11]([CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[S:27]([CH2:25][CH3:26])(=[O:29])=[O:28]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 11667Ethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 198448423-(2,4-Difluorophenylaminomethyl)pyridine chloromethane

Product 1

HCID 14720331N-(2,4-difluorophenyl)-N-(pyridin-3-ylmethyl)ethanesulfonamide

Procedure

A 4.4 g. portion of 3-(2,4-difluorophenylaminomethyl)pyridine chloromethane, and 4.1 g. of potassium carbonate and 3.9 g. of ethanesulfonyl chloride were added. The mixture was stirred under reflux for several days. It was then diluted with 20 ml. of aqueous sodium bicarbonate and 20 ml. of dichloromethane, and the organic phase was dried and evaporated to an oil. The oil was dissolved in dichloromethane and chromatographed over silica gel, eluting with dichloromethane, to obtain 1.2 g. of the desired product, after triturating with diethyl ether and petroleum ether. M.P. 91°-92°.

Workup

  1. temperatureunder reflux for several days
  2. additionIt was then diluted with 20 ml
  3. dry with materialof dichloromethane, and the organic phase was dried
  4. customevaporated to an oil
  5. dissolutionThe oil was dissolved in dichloromethane
  6. customchromatographed over silica gel
  7. washeluting with dichloromethane
  8. customto obtain 1.2 g
  9. customof the desired product, after triturating with diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-591049fea23340ada6543bf107c543b7
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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