Potassium Carbonate → HCID 14720343, compound

HRID 2352001Notes

Reaction equation

HRID 2352001 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[NH:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[N:11]([CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[S:26]([CH3:25])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 14720342N-(2,4-Dimethoxyphenyl)-3-pyridinemethanamine

Product 1

HCID 14720343HCID 14720343, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 7.3 g. portion of 3-(2,4-dimethoxyphenylaminomethyl)pyridine was dissolved in 25 ml. of dichloromethane, and 5.5 g. of potassium carbonate and 3.1 ml. of methanesulfonyl chloride were added. The mixture was stirred under reflux overnight. Then it was cooled, diluted with 25 ml. of dichloromethane and washed with 25 ml. of aqueous sodium bicarbonate. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated under vacuum. The residue was suspended in ethyl acetate, and filtered. The filtrate was evaporated, and the residue was triturated with diethyl ether, filtered and dried under vacuum to obtain 6.7 g. of the desired product, m.p. 117°-119°.

Workup

  1. temperatureunder reflux overnight
  2. temperatureThen it was cooled
  3. additiondiluted with 25 ml
  4. washof dichloromethane and washed with 25 ml
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under vacuum
  9. filtrationfiltered
  10. customThe filtrate was evaporated
  11. customthe residue was triturated with diethyl ether
  12. filtrationfiltered
  13. customdried under vacuum
  14. customto obtain 6.7 g

Sources & evidence

ORD record
ord-2624d6f2c52d4c9bb8306927f1ffd516
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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