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

HRID 1665228
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HRID 1665228 반응식
[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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 7237O-Xylene용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4156e820019b42d6a64b96a7c41f8f71
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08039500B2

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