Imidazole → N,N-Dimethyl-1H-imidazole-1-sulfonamide

HRID 31542Notes

Reaction equation

HRID 31542 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.[CH3:13][N:14]([CH3:19])[S:15](Cl)(=[O:17])=[O:16]>C1(C)C=CC=CC=1>[CH3:13][N:14]([CH3:19])[S:15]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 395751N,N-Dimethyl-1H-imidazole-1-sulfonamideYield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Imidazole (5.00 g, 73.6 mmol) was dissolved in toluene (80 ml), and thereto were added triethylamine (9.52 ml, 68.4 mmol) and dimethylsulfamoyl chloride (6.77 ml, 63.3 mmol), and the mixture was stirred at room temperature for 8 hours. The precipitates were removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to azeotropic distillation with hexane to give the title compound (10.9 g, 98%).

Workup

  1. customThe precipitates were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. distillationThe resulting residue was subjected to azeotropic distillation with hexane

Sources & evidence

ORD record
ord-cdd939ed61584f64924ac03c476e701c
Source dataset
uspto-grants-2008_09
Patent number
US07425642B2

Reaction notes

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