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

HRID 899640노트

반응식

HRID 899640 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

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, 11H).

후처리

  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)

출처 및 근거

ORD 기록
ord-1ac032bb9a7441fca10eca4b3d93c50c
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354932B2

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