Potassium Carbonate → HCID 14720349, compound

HRID 2352004Notes

Reaction equation

HRID 2352004 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]([O:16][CH3:17])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>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:25]([CH3:24])(=[O:27])=[O:26])=[C:4]([O:16][CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 14720348HCID 14720348, compound

Product 1

HCID 14720349HCID 14720349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2.5 g. portion of 3-(4-chloro-2-methoxyphenylaminomethyl)pyridine was dissolved in 20 ml. of dichloromethane, and to it were added 2.1 g. of potassium carbonate and 1.2 ml. of methanesulfonyl chloride. The mixture was stirred with gentle heating for 2 days, and was then extracted with aqueous sodium bicarbonate. The organic phase was dried and evaporated under vacuum, and the residue was redissolved in dichloromethane and 2.6 g. of methanesulfonic anhydride was added. The mixture was stirred at ambient temperature for several days, and another 2.6 g. of the anhydride was added, together with 2.5 g. of additional starting amine. The mixture was stirred at ambient temperature for several days more, and was then diluted with 20 ml. of aqueous sodium bicarbonate and 15 ml. of dichloromethane, and the organic phase was dried over magnesium sulfate and evaporated to an oil. The oil was taken up in chloroform and chromatographed over silica gel, eluting with chloroform, to obtain 1.17 g. of the desired compound, m.p. 121°-123°.

Workup

  1. temperaturewith gentle heating for 2 days
  2. extractionwas then extracted with aqueous sodium bicarbonate
  3. customThe organic phase was dried
  4. customevaporated under vacuum
  5. dissolutionthe residue was redissolved in dichloromethane
  6. additionof methanesulfonic anhydride was added
  7. stirringThe mixture was stirred at ambient temperature for several days
  8. additionof the anhydride was added, together with 2.5 g
  9. stirringThe mixture was stirred at ambient temperature for several days more
  10. additionwas then diluted with 20 ml
  11. dry with materialof dichloromethane, and the organic phase was dried over magnesium sulfate
  12. customevaporated to an oil
  13. customchromatographed over silica gel
  14. washeluting with chloroform
  15. customto obtain 1.17 g

Sources & evidence

ORD record
ord-48b279238c06418aa03781cc83a433d9
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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