Triethylamine → N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide

HRID 216357Notes

Reaction equation

HRID 216357 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:14])[S:10](Cl)(=[O:12])=[O:11].[CH3:15][C:16]([C:25]([F:28])([F:27])[F:26])([CH:23]=[CH2:24])[CH2:17][C:18]1[N:19]=[CH:20][NH:21][CH:22]=1>C(Cl)Cl.O>[CH3:8][N:9]([CH3:14])[S:10]([N:21]1[CH:22]=[C:18]([CH2:17][C:16]([CH3:15])([C:25]([F:26])([F:27])[F:28])[CH:23]=[CH2:24])[N:19]=[CH:20]1)(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 178442249HCID 178442249, compound

Product 1

HCID 59140382N,N-dimethyl-4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (3 mL, 14.02 mmol) followed by dimethylsulfamoyl chloride (1.5 mL, 14.02 mmol) were added to an ambient temperature solution of 4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole (1.43 g, 7.01 mmol) in methylene chloride (20 mL). After stirring at ambient temperature overnight, the reaction mixture was diluted with water and extracted with ethyl acetate and methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl aceate/hexane afforded the title compound.

Workup

  1. extractionextracted with ethyl acetate and methylene chloride
  2. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3dddb409e81e4c889818fe52fd4a3c03
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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