Water → 1-Dimethylsulfamoyl-2-ethylimidazole

HRID 326469

Reaction equation

HRID 326469 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 thereto and the organic layer is separated therefrom and concentrated. The residue is dissolved in ethyl acetate (1 liter) and washed with water. The solution is dried over sodium sulfate and concentrated. Distillation gives 1-dimethylsulfamoyl-2-ethylimidazole (182 g) as colorless liquid.

Workup

  1. customthe organic layer is separated
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in ethyl acetate (1 liter)
  4. washwashed with water
  5. dry with materialThe solution is dried over sodium sulfate
  6. concentrationconcentrated
  7. distillationDistillation

Sources & evidence

ORD record
ord-a39ea9eac1b64affa0731f5f0d09ece4
Source dataset
uspto-grants-1993_12
Patent number
US05268377

Linked notes

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