Potassium Carbonate → Methanesulfonamide, N-(2,4-difluorophenyl)-N-(3-pyridinylmethyl)-

HRID 2351969Notes

Reaction equation

HRID 2351969 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+].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>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:24]([CH3:23])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 110961292,4-difluoro-N-(pyridin-3-ylmethyl)aniline

Product 1

HCID 188740Methanesulfonamide, N-(2,4-difluorophenyl)-N-(3-pyridinylmethyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 8.9 g. portion of 3-(2,4-difluorophenylaminomethyl)pyridine was dissolved in 30 ml. of dichloromethane, and to it was added 6.9 g. of potassium carbonate and 3.9 ml. of methanesulfonyl chloride. The mixture was stirred at ambient temperature for several days, and then was heated and stirred at the reflux temperature overnight. It was then cooled, extracted with aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated to a small volume. The residue was chromatographed over silica gel, eluting first with dichloromethane and then with 9:1 dichloromethane:ethyl acetate. The product-containing fractions were combined and evaporated to obtain impure product, which was triturated with diethyl ether and dried to obtain 5.6 g. of the desired product, m.p. 132°-135°.

Workup

  1. temperaturewas heated
  2. stirringstirred at the reflux temperature overnight
  3. temperatureIt was then cooled
  4. extractionextracted with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to a small volume
  7. customThe residue was chromatographed over silica gel
  8. washeluting first with dichloromethane
  9. customevaporated
  10. customto obtain impure product, which
  11. customwas triturated with diethyl ether
  12. customdried
  13. customto obtain 5.6 g

Sources & evidence

ORD record
ord-9b57a4607bec49f8b0821b1f1370e23c
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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