Potassium Carbonate → HCID 14720293, compound

HRID 2351974Notes

Reaction equation

HRID 2351974 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[S:30]([CH3:29])(=[O:32])=[O:31])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 14720292HCID 14720292, compound

Product 1

HCID 14720293HCID 14720293, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.5 g. portion of 3-(4-cyclohexylmethoxyphenylaminomethyl)pyridine was dissolved in 15 ml. of dichloromethane, and 2.76 g. of potassium carbonate and 1.55 ml. of methanesulfonyl chloride were added. The mixture was stirred with gentle heating for 20 hours, and was then extracted with aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated under vacuum. The residue was dissolved in chloroform and chromatographed over silica gel, eluting with chloroform. The product-containing fractions were combined and evaporated, and the residue was triturated with diethyl ether, filtered and dried to obtain 2.33 g. of impure product, which was further washed with diethyl ether to obtain 1.88 g. of the desired product, m.p. 36°-140°.

Workup

  1. temperaturewith gentle heating for 20 hours
  2. extractionwas then extracted with aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum
  5. dissolutionThe residue was dissolved in chloroform
  6. customchromatographed over silica gel
  7. washeluting with chloroform
  8. customevaporated
  9. customthe residue was triturated with diethyl ether
  10. filtrationfiltered
  11. customdried
  12. customto obtain 2.33 g
  13. washof impure product, which was further washed with diethyl ether
  14. customto obtain 1.88 g

Sources & evidence

ORD record
ord-3b28eb96dfde4049bd3074c1d559ab49
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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