Potassium Carbonate → HCID 14720326, compound

HRID 2351992Notes

Reaction equation

HRID 2351992 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(=O)(O)[O-].[Na+].[OH-].[Na+]>ClCCl.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:10][C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1)[S:24]([CH3:23])(=[O:26])=[O:25]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 14720325N-(2,4-Difluorophenyl)-4-pyridinemethanamine

Product 1

HCID 14720326HCID 14720326, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A 4.7 g. portion of 4-(2,4-difluorophenylaminomethyl)pyridine was dissolved in 15 ml. of chloroform, and 4.1 g. of potassium carbonate was added, followed by 2.3 ml. of methanesulfonyl chloride. The mixture was stirred under reflux overnight, and then for several days at ambient temperature. It was then diluted with 20 ml. of dichloromethane and 20 ml. of aqueous sodium bicarbonate, and 5 ml. of 2N sodium hydroxide was added. The organic phase was then washed with aqueous sodium bicarbonate, dried and evaporated. The residue was dissolved in dichloromethane and chromatographed over silica gel, to obtain 0.5 g. of impure product, which was triturated with diethyl ether to obtain 0.29 g. of the desired product, m.p. 101°-105°.

Workup

  1. temperatureunder reflux overnight
  2. waitfor several days at ambient temperature
  3. additionIt was then diluted with 20 ml
  4. washThe organic phase was then washed with aqueous sodium bicarbonate
  5. customdried
  6. customevaporated
  7. dissolutionThe residue was dissolved in dichloromethane
  8. customchromatographed over silica gel
  9. customto obtain 0.5 g
  10. customof impure product, which was triturated with diethyl ether
  11. customto obtain 0.29 g

Sources & evidence

ORD record
ord-11afd315273f48078ffc5ac7aef89735
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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