Potassium Carbonate → HCID 14720308, compound

HRID 2351981Notes

Reaction equation

HRID 2351981 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[S:23]([CH3:22])(=[O:25])=[O:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chloride2×HCID 6395044-Chloro-N-[(pyridin-2-yl)methyl]aniline

Product 1

HCID 14720308HCID 14720308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.3 g. portion of 2-(4-chlorophenylaminomethyl)pyridine was dissolved in 15 ml. of dichloromethane, and 2.7 g. of potassium carbonate and 1.5 ml. of methanesulfonyl chloride were added. The mixture was stirred overnight at ambient temperature, and then was stirred for 1 day under gentle reflux. Another 0.5 ml. of methanesulfonyl chloride was added, and the reflux was continued for several hours. Then the mixture was cooled and filtered, and the filtrate was chromatographed on a silica gel column, eluting with chloroform. The product-containing fractions were combined and evaporated to obtain 1 g. of the desired product.

Workup

  1. stirringwas stirred for 1 day under gentle reflux
  2. waitthe reflux was continued for several hours
  3. temperatureThen the mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate was chromatographed on a silica gel column
  6. washeluting with chloroform
  7. customevaporated
  8. customto obtain 1 g

Sources & evidence

ORD record
ord-46f2b7fd9fbd433fbf62da70df96b29f
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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