Potassium Carbonate → HCID 14720289, compound

HRID 2351972Notes

Reaction equation

HRID 2351972 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:9]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:11][CH2:12][CH3:13])[S:27]([CH3:26])(=[O:29])=[O:28])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chloride2×HCID 14720288HCID 14720288, compound

Product 1

HCID 14720289HCID 14720289, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 5.5 g. portion of 3-[1-(4-fluorophenylamino)pentyl]pyridine was dissolved in 40 ml. of dichloromethane, and to it were added 3.4 g. of potassium carbonate and 1.9 ml. of methanesulfonyl chloride. The mixture was stirred at ambient temperature overnight, and then an additional 1.9 ml. of methanesulfonyl chloride was added and the mixture was stirred for 3 days with gentle heating. It was then cooled and extracted with aqueous sodium bicarbonate solution, and then with water, and it was then dried over magnesium sulfate and evaporated under vacuum. The residue was dissolved in chloroform and was purified over silica gel, eluting with chloroform, to obtain 0.7 g. of the desired product.

Workup

  1. stirringthe mixture was stirred for 3 days with gentle heating
  2. temperatureIt was then cooled
  3. extractionextracted with aqueous sodium bicarbonate solution
  4. dry with materialwith water, and it was then dried over magnesium sulfate
  5. customevaporated under vacuum
  6. dissolutionThe residue was dissolved in chloroform
  7. customwas purified over silica gel
  8. washeluting with chloroform
  9. customto obtain 0.7 g

Sources & evidence

ORD record
ord-c161e50d562e48d7b95fc2b90a259cf6
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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