Potassium Carbonate → N-(2,4-difluorophenyl)-N',N'-dimethyl-N-(pyridin-3-ylmethyl)sulfamide

HRID 2351993Notes

Reaction equation

HRID 2351993 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:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:23][N:24]([CH3:29])[S:25](Cl)(=[O:27])=[O:26]>ClCCl>[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]=[N:13][CH:14]=[CH:15][CH:16]=1)[S:25]([N:24]([CH3:29])[CH3:23])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 83372Dimethylsulphamoyl chlorideHCID 110961292,4-difluoro-N-(pyridin-3-ylmethyl)aniline

Product 1

HCID 14720327N-(2,4-difluorophenyl)-N',N'-dimethyl-N-(pyridin-3-ylmethyl)sulfamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.3 g. portion of 3-(2,4-difluorophenylaminomethyl)pyridine was dissolved in 15 ml. of dichloromethane, and 2.8 g. of potassium carbonate and 3.6 g. of dimethylsulfamoyl chloride were added. The mixture was stirred at ambient temperature for several days, and was then stirred under reflux for 4 hours. The mixture was then cooled, and extracted with 20 ml. of aqueous sodium bicarbonate and with 20 ml. of water, and was dried and evaporated to an oil. The oil was dissolved in dichloromethane and chromatographed over silica gel, eluting with 9:1 dichloromethane:ethyl acetate to obtain 2.1 g. of the desired product.

Workup

  1. stirringwas then stirred
  2. temperatureunder reflux for 4 hours
  3. temperatureThe mixture was then cooled
  4. extractionextracted with 20 ml
  5. dry with materialof water, and was dried
  6. customevaporated to an oil
  7. dissolutionThe oil was dissolved in dichloromethane
  8. customchromatographed over silica gel
  9. washeluting with 9:1 dichloromethane
  10. customethyl acetate to obtain 2.1 g

Sources & evidence

ORD record
ord-d26fbcb5ec9944fdb418b4f93f1670c5
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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