Water → 1-Dimethylsulfamoyl-2-ethylimidazole

HRID 21882

Reaction equation

HRID 21882 reaction equation
[CH2:1]([C:3]1[NH:4][CH:5]=[CH:6][N:7]=1)[CH3:2].C(N(CC)CC)C.[CH3:15][N:16]([CH3:21])[S:17](Cl)(=[O:19])=[O:18].O>C(Cl)(Cl)Cl>[CH3:15][N:16]([CH3:21])[S:17]([N:4]1[CH:5]=[CH:6][N:7]=[C:3]1[CH2:1][CH3:2])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 661302-EthylimidazoleHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 232931831-Dimethylsulfamoyl-2-ethylimidazoleYield 86.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 2-ethylimidazole (100 g) and triethylamine (115 g) in chloroform (800 ml) at 0° C. is added a solution of dimethylsulfamoyl chloride (153 g) in chloroform (200 ml). The mixture is stirred overnight at room temperature. Water (1.5 liter) is added to the reaction mixture after which the organic layer is separated and concentrated. The residue is dissolved in ethyl acetate (1 liter) and washed with water, and then dried over sodium sulfate and concentrated. Distillation gives 1-dimethylsulfamoyl-2-ethylimidazole (182 g) as a colorless liquid.

Workup

  1. customis separated
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in ethyl acetate (1 liter)
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. distillationDistillation

Sources & evidence

ORD record
ord-61bc5d6024df4362ad3eac19e9288450
Source dataset
uspto-grants-1995_06
Patent number
US05424316

Linked notes

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