Potassium Carbonate → HCID 14720324, compound

HRID 2351991Notes

Reaction equation

HRID 2351991 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[S:23]([CH3:22])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 14720323HCID 14720323, compound

Product 1

HCID 14720324HCID 14720324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 10 g. portion of 3-(2-methylphenylaminomethyl)pyridine was dissolved in 100 ml. of dichloromethane, and 10 g. of potassium carbonate and 8 g. of methanesulfonyl chloride were added. The mixture was stirred at ambient temperature for 3 days, and was then diluted with 200 ml. of dichloromethane and extracted twice with 100 ml. portions of water. The organic phase was dried over magnesium sulfate and evaporated to an oil, which was chromatographed over silica gel with 1:4 acetone:toluene. The product-containing fractions were combined and evaporated, and the residue solidified upon standing and was recrystallized from hot diethyl ether to obtain 2.9 g. of the desired product, m.p. 97°-98°.

Workup

  1. additionwas then diluted with 200 ml
  2. extractionof dichloromethane and extracted twice with 100 ml
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customevaporated to an oil, which
  5. customwas chromatographed over silica gel with 1:4 acetone
  6. customevaporated
  7. customwas recrystallized from hot diethyl ether
  8. customto obtain 2.9 g

Sources & evidence

ORD record
ord-3e9da93911a94bd799ab27397149a7d0
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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