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Tetrahydrofuran → N-Acetyl-3,4-bis(heptyloxy)-N-(2-pyridinylmethyl)benzamide

HRID 248015
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HRID 248015 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:12](Cl)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].[Na+].[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][NH:35][C:36](=[O:38])[CH3:37].O1CCCC1>O>[C:36]([N:35]([CH2:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=1)[C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:9]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:10]=1)(=[O:38])[CH3:37]
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참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 5084090N-(pyridin-2-ylmethyl)acetamideHCID 190151863,4-Bis(heptyloxy)benzoyl chloride

생성물 1

HCID 10367999N-Acetyl-3,4-bis(heptyloxy)-N-(2-pyridinylmethyl)benzamide수율 44.8%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

The title compound is prepared by the procedure of Example 27 using 5.0 g of product from Example 111, 0.683 g of washed 50% sodium hydride, 2.14 g of product from Example 12 and 100 ml of dry tetrahydrofuran. The reaction is stirred at room temperature for 1 hour, heated at reflux temperature for 18 hours and cooled to room temperature. The mixture is poured into water, extracted with chloroform and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 15-30% ethyl acetate/hexane) to give 2.93 g of the desired product.

후처리

  1. temperatureheated
  2. temperatureat reflux temperature for 18 hours
  3. temperaturecooled to room temperature
  4. extractionextracted with chloroform
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography (silica gel: 15-30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-0bd7858628244defa554613b343fb739
출처 데이터셋
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05208247

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