Potassium Carbonate → HCID 19844921, compound

HRID 2351968Notes

Reaction equation

HRID 2351968 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[CH2:4][N:5]([CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[S:25]([CH3:24])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 913930HCID 913930, compound

Product 1

HCID 19844921HCID 19844921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.2 g. portion of 3-(2,4-dichlorobenzylaminomethyl)pyridine was dissolved in 15 ml. of dichloromethane, and to it was added 2 g. of potassium carbonate and 1.16 ml. of methanesulfonyl chloride. The mixture was stirred at ambient temperature for several days, and was then extracted twice with 15 ml. portions of water, dried, filtered, and evaporated under vacuum to an oil. The residue was dissolved in chloroform and purified over silica gel, eluting first with chloroform and then with 9:1 chloroform:acetone. The product-containing fractions were combined and evaporated under vacuum to obtain 2.9 g. of impure product, which was triturated with petroleum ether to obtain 2.1 g. of the desired product, m.p. 78°-80°.

Workup

  1. extractionwas then extracted twice with 15 ml
  2. dry with materialportions of water, dried
  3. filtrationfiltered
  4. customevaporated under vacuum to an oil
  5. dissolutionThe residue was dissolved in chloroform
  6. custompurified over silica gel
  7. washeluting first with chloroform
  8. customevaporated under vacuum
  9. customto obtain 2.9 g
  10. customof impure product, which was triturated with petroleum ether
  11. customto obtain 2.1 g

Sources & evidence

ORD record
ord-9d55254fc34b4370bb4e32cd4fe6e769
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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