Potassium Carbonate → N-(4-Fluorophenyl)-N-[1-(pyridin-3-yl)ethyl]methanesulfonamide

HRID 2351960Notes

Reaction equation

HRID 2351960 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])[S:24]([CH3:23])(=[O:26])=[O:25])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chloride2×HCID 14720275HCID 14720275, compound

Product 1

HCID 163901N-(4-Fluorophenyl)-N-[1-(pyridin-3-yl)ethyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 10.8 g. portion of 3-[1-(4-fluorophenylamino)ethyl]pyridine was dissolved in 50 ml. of dichloromethane and 10.4 g. of potassium carbonate was added, followed by 5.9 ml. of methanesulfonyl chloride. The mixture was stirred for two days at ambient temperature, 1.8 ml. more methanesulfonyl chloride was added, and the mixture was then stirred under gentle reflux for four days. It was then cooled, extracted twice with water, dried and concentrated to an oil. The oil was dissolved in dichloromethane and chromatographed on silica gel, eluting with dichloromethane, then with chloroform, and finally with chloroform:acetone to obtain 10.7 g. of oily product. It crystallized upon seeding, m.p. 82°-85°.

Workup

  1. stirringthe mixture was then stirred
  2. temperatureunder gentle reflux for four days
  3. temperatureIt was then cooled
  4. extractionextracted twice with water
  5. customdried
  6. concentrationconcentrated to an oil
  7. dissolutionThe oil was dissolved in dichloromethane
  8. customchromatographed on silica gel
  9. washeluting with dichloromethane
  10. customwith chloroform, and finally with chloroform:acetone to obtain 10.7 g
  11. customIt crystallized

Sources & evidence

ORD record
ord-b9e824dce52440bba8952e9326ca4688
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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