Triethylamine → 2-Cyclopropyl-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 1488126

반응식

HRID 1488126 반응식
[CH:1]1([C:4]2[NH:5][CH:6]=[CH:7][N:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:16][N:17]([CH3:22])[S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH:1]1([C:4]2[N:5]([S:18]([N:17]([CH3:22])[CH3:16])(=[O:20])=[O:19])[CH:6]=[CH:7][N:8]=2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 179423832-cyclopropyl-1H-imidazole2회

생성물 1

HCID 900310182-Cyclopropyl-N,N-dimethyl-1H-imidazole-1-sulfonamide수율 67%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Into a 500-mL round-bottom flask, was placed a solution of 2-cyclopropyl-1H-imidazole (compound 238.1, 12 g, 110.9 mmol) in dichloromethane (60 mL). Triethylamine (31.4 mL, 225.3 mmol), N,N-dimethylsulfamoyl chloride (13.2 mL, 121.87 mmol, 1.10 equiv) were added to the reaction. The reaction mixture was stirred for 4 h at room temperature, then quenched with 20 mL of water. The aqueous phase was extracted with 3×100 mL of dichloromethane. The combined organic layers were washed with 2×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:4) as eluent to furnish 16 g (67%) of the title compound as a white solid.

후처리

  1. customInto a 500-mL round-bottom flask, was placed
  2. customquenched with 20 mL of water
  3. extractionThe aqueous phase was extracted with 3×100 mL of dichloromethane
  4. washThe combined organic layers were washed with 2×20 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:4) as eluent

출처 및 근거

ORD 기록
ord-bbd2b4459d024dd4929d473a690bb4a7
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428502B2

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