1-Heptyl-1H-imidazole → 1-[3-((2,6-Dimethylphenyl)sulfamoyl)propyl]-3-heptylimidazolium chloride

HRID 65244Notes

Reaction equation

HRID 65244 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Cl:13][CH2:14][CH2:15][CH2:16][S:17]([NH:20][C:21]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:28])(=[O:19])=[O:18]>O>[Cl-:13].[CH3:28][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([CH3:27])[C:21]=1[NH:20][S:17]([CH2:16][CH2:15][CH2:14][N+:10]1[CH:11]=[CH:12][N:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:9]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 1866691-Heptyl-1H-imidazoleHCID 201883713-chloro-N-(2,6-dimethylphenyl)propanesulfonamide

Product 1

HCID 867410301-[3-((2,6-Dimethylphenyl)sulfamoyl)propyl]-3-heptylimidazolium chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 15.0 g (0.0919 mole) 1-heptyl-1H-imidazole and 25.5 g (0.0974 mole) 3-chloro-N-(2,6-dimethylphenyl)propanesulfonamide and heat for about 24 hours at 130° C. Follow the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile: ammonium hydroxide, 9:1). At the completion of the reaction, dissolve the resulting cooled oil in 500 ml H2O. Extract the resultant solution with 6×500 ml hexane. Extract aqueous layer with 3×500 ml CH2Cl2. Wash combined CH2Cl2 layers 1×250 ml saturated NaCl solution. Dry the methylene chloride solution over Na2SO4. Evaporate the CH2Cl2 to provide the title compound as an oil. Triturate the oil with Et2O to provide solid. Recrystallize by dissolving the solid in a minimum of hot acetone. Seed and chill the solution to provide white crystals.

Workup

  1. customthe progress of the reaction by thin-layer chromatography on silica gel (acetonitrile: ammonium hydroxide, 9:1)
  2. customAt the completion of the reaction
  3. dissolutiondissolve the resulting
  4. extractionExtract the resultant solution with 6×500 ml hexane
  5. washWash
  6. dry with materialDry the methylene chloride solution over Na2SO4
  7. customEvaporate the CH2Cl2

Sources & evidence

ORD record
ord-41969ff810974d79848dd8f589f1f22c
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Reaction notes

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