Dichloromethane → 2-Butyl-3-dimethylaminosulfonylimidazole

HRID 365936Notes

Reaction equation

HRID 365936 reaction equation
[CH2:1]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[CH3:10][N:11]([CH3:16])[S:12](Cl)(=[O:14])=[O:13].C(Cl)Cl.C(N(CC)CC)C>O>[CH2:1]([C:5]1[N:9]([S:12]([N:11]([CH3:16])[CH3:10])(=[O:14])=[O:13])[CH:8]=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 118153512-butyl-1H-imidazole

Product 1

HCID 232931822-Butyl-3-dimethylaminosulfonylimidazoleYield 103.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

12.4 g of butylimidazole and 13.3 g of N,N-dimethylsulfamoyl chloride were introduced into 200 ml of methylene chloride, and 9.7 g of triethylamine was added at room temperature. The mixture was stirred for 20 hours at room temperature and for 2 hours at 40° C., 200 ml of water was added and the phases were separated. The organic phase was washed with water, dried with Na2SO4 and concentrated by evaporation to give 22.2 g of product in the form of a red oil. The yield was 96 percent. Other data concerning the product was:

Workup

  1. additionwas added at room temperature
  2. customthe phases were separated
  3. washThe organic phase was washed with water
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1d438c20152440278d27a757ac9b6d05
Source dataset
uspto-grants-2000_10
Patent number
US06127548

Reaction notes

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