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

HRID 2351990Notes

Reaction equation

HRID 2351990 reaction equation
[Cl: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)=[C:4]([CH3:16])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(=O)(O)[O-].[Na+].[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[S:24]([CH3:23])(=[O:26])=[O:25])=[C:4]([CH3:16])[CH:3]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 14720322HCID 14720322, compound

Product 1

HCID 163902Methanesulfonamide, N-(4-chloro-2-methylphenyl)-N-(3-pyridinylmethyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 2.4 g. portion of 3-(4-chloro-2-methylphenylaminomethyl)pyridine was dissolved in 15 ml. of dichloromethane, and 2.1 g. of potassium carbonate and 2 ml. of methanesulfonyl chloride were added. The mixture was stirred at ambient temperature for several days, and then under reflux for another day. It was then cooled and diluted with 20 ml. of aqueous sodium bicarbonate and 5 ml. of 2N sodium hydroxide, 20 ml. of dichloromethane was added, and the organic layer was washed with aqueous sodium bicarbonate, dried and evaporated to an oil. The oil was dissolved in dichloromethane and chromatographed over silica gel, eluting first with dichloromethane and then with dichloromethane:ethyl acetate. The product-containing fractions were combined to obtain 1.8 g. of the desired product.

Workup

  1. temperatureunder reflux for another day
  2. temperatureIt was then cooled
  3. additiondiluted with 20 ml
  4. washthe organic layer was washed with aqueous sodium bicarbonate
  5. customdried
  6. customevaporated to an oil
  7. dissolutionThe oil was dissolved in dichloromethane
  8. customchromatographed over silica gel
  9. washeluting first with dichloromethane
  10. customto obtain 1.8 g

Sources & evidence

ORD record
ord-0f7138c799a84c0492575c791baa29a4
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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