Triethylamine → N,N-Dimethyl-4,5,6,7-tetrahydro-1H-benzimidazole-1-sulfonamide

HRID 1624285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1624285
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[CH:2]1.C(N(CC)CC)C.[CH3:17][N:18]([CH3:23])[S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:17][N:18]([CH3:23])[S:19]([N:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[CH:2]1)(=[O:21])=[O:20]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 3042634,5,6,7-Tetrahydro-1H-benzimidazole

Produkt 1

HCID 69156673N,N-Dimethyl-4,5,6,7-tetrahydro-1H-benzimidazole-1-sulfonamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To solution of 4,5,6,7-tetrahydro-1H-benzoimidazole (1.9992 g, 16.4 mmol) and triethylamine (4.60 mL, 32.8 mmol) in CH2Cl2 (20 mL) at 0° C. was added dropwise a solution of dimethyl sulfamoyl chloride (1.76 mL, 16.4 mmol) in CH2Cl2 (10 mL). The reaction was warmed to room temperature and stirred for 3.5 hours. CH2Cl2 (80 mL) was added and the organic phase was washed with distilled water (1×80 mL). The aqueous washing was extracted with CH2Cl2 (2×40 mL), and the combined organic extracts were washed with brine (1×80 mL), dried (Na2SO4), and concentrated. Purification of the crude material by column chromatography on silica gel (2:1 hexanes-EtOAc) provided 2.89 g (77%) of 4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide as a white solid. 1H NMR (CDCl3) δ 1.77-1.86 (m, 4H), 2.58-2.61 (m, 2H), 2.72 (t, 2H, J=6 Hz), 2.87 (s, 6H), 7.77 (s, 1H).

Aufarbeitung

  1. washthe organic phase was washed with distilled water (1×80 mL)
  2. washThe aqueous washing
  3. extractionwas extracted with CH2Cl2 (2×40 mL)
  4. washthe combined organic extracts were washed with brine (1×80 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification of the crude material by column chromatography on silica gel (2:1 hexanes-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-0715ee709d3d41f2a9b614b85607ae75
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778967B2

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