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

HRID 2269171Notes

Reaction equation

HRID 2269171 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]>C1C=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-sulfonamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Imidazole (1) (20.0 g, 0.29 mol), triethylamine (41.0 mL, 0.29 mol) and N,N-dimethylsulfamoyl chloride (31.6 mL, 0.29 mol) were added to 320 mL of benzene. The reaction was stirred for 48 h at room temperature (rt) and then filtered. The filtrate was collected and concentrated under reduced pressure. Vacuum distillation of the crude product (˜0.5 mmHg, 115°-118° C.) afforded 38.7 g (76%) of a clear and colorless oil. Upon cooling the product solidifies to give white crystals (2). 1-(Dimethylsulfamoyl) imidazole (2) (18.8 g, 0.11 mol) was added to 430 mL of tetrahydrofuran THF). The solution was cooled to −78° C. A solution of n-butyl lithium (n-BuLi) in hexane (1.6M, 70.9 mL, 0.11 mol) was added dropwise to the reaction flask. Upon completion, the reaction was stirred for 1 h at −78° C. t-Butyldimethylsilylchloride (17.8 g, 0.12 mol) in 50 mL of THF was added via cannula to the reaction. After the addition was completed the reaction mixture was warmed slowly to rt and then stirred for 24 h. The reaction was diluted with water and the organic layer separated. The organic phase was washed with brine and then dried over sodium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure. Column chromatography (20% ethyl acetate/hexane as eluant) afforded a light yellow solid. Recrystallization from pentane gave 30 g (94%) of white crystals (3).

Workup

  1. filtrationfiltered
  2. customThe filtrate was collected
  3. concentrationconcentrated under reduced pressure
  4. distillationVacuum distillation of the crude product (˜0.5 mmHg, 115°-118° C.)
  5. customafforded 38.7 g (76%) of a clear and colorless oil
  6. temperatureUpon cooling the product

Sources & evidence

ORD record
ord-378e716dc83a438f997cf9a0c9d15ea2
Source dataset
uspto-grants-2001_12
Patent number
US06329369B1

Reaction notes

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