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

HRID 1624285ノート

反応式

HRID 1624285 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0715ee709d3d41f2a9b614b85607ae75
出典データセット
uspto-grants-2014_07
特許番号
US08778967B2

反応ノート

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