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p-Toluenesulfonic acid monohydrate → 7-[1-Ethylprop-1-en-1-yl]-2-(mesitylmethyl)-1-methyl-1H-benzimidazole

HRID 1665228
ノート
印刷プレビュー

反応式

HRID 1665228 の反応式
[C:1]1([CH3:26])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]([C:20](O)([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[CH2:23]([C:20]([C:16]1[C:13]2[N:14]([CH3:15])[C:10]([CH2:9][C:2]3[C:1]([CH3:26])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=3[CH3:8])=[N:11][C:12]=2[CH:19]=[CH:18][CH:17]=1)=[CH:21][CH3:22])[CH3:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 249864303-[2-(Mesitylmethyl)-1-methyl-1H-benzimidazol-7-yl]pentan-3-ol

生成物 1

HCID 674389407-[1-Ethylprop-1-en-1-yl]-2-(mesitylmethyl)-1-methyl-1H-benzimidazole

試薬・触媒・溶媒 2

HCID 7237O-Xylene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 3-[2-(mesitylmethyl)-1-methyl-1H-benzimidazol-7-yl]pentan-3-ol (200 mg, 0.571 mmol) and p-toluenesulfonic acid monohydrate (326 mg, 1.71 mmol) in xylene (10 mL) was refluxed for 3 hr. After cooling, the mixture was diluted with ethyl acetate (50 mL) and washed with saturated aqueous sodium bicarbonate solution (30 mL) and brine (30 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 10-20% ethyl acetate/n-hexane gradient mixture to give the title compound (180 mg, 0.542 mmol, 95%, as a mixture of geometric isomers) as a colorless solid.

後処理

  1. temperatureAfter cooling
  2. washwashed with saturated aqueous sodium bicarbonate solution (30 mL) and brine (30 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with 10-20% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-4156e820019b42d6a64b96a7c41f8f71
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08039500B2

反応ノート

読み込み中…

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