Potassium Carbonate → HCID 14720311, compound

HRID 2351983Notes

Reaction equation

HRID 2351983 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:23][N:24]([CH3:29])[S:25](Cl)(=[O:27])=[O:26]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])[S:25]([N:24]([CH3:29])[CH3:23])(=[O:27])=[O:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 83372Dimethylsulphamoyl chlorideHCID 13652428HCID 13652428, compound

Product 1

HCID 14720311HCID 14720311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.5 g. portion of 3-[1-(4-chlorophenylamino)ethyl]pyridine was dissolved in dichloromethane and 2.7 g. of potassium carbonate and 2.9 g. of dimethylsulfamoyl chloride were added. The mixture was stirred at ambient temperature for 3 days, and was then diluted with 25 ml. of additional dichloromethane and was extracted with water. The organic layer was dried over magnesium sulfate and evaporated to an oil, which was taken up in dichloromethane and chromatographed over silica gel, eluting with chloroform. The product-containing fractions were combined and evaporated to obtain about 0.3 g. of the desired product.

Workup

  1. additionwas then diluted with 25 ml
  2. extractionof additional dichloromethane and was extracted with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated to an oil, which
  5. customchromatographed over silica gel
  6. washeluting with chloroform
  7. customevaporated
  8. customto obtain about 0.3 g

Sources & evidence

ORD record
ord-dc9ad2bb2dcd440abac7e1d37cd1e976
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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