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4-Toluenesulfonyl chloride → 2,2,4,6,7-Pentamethyl-5-(p-toluenesulfonylamino)-2,3-dihydrobenzofuran

HRID 2260678
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HRID 2260678 반응식
[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([CH3:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[C:12]=1[CH3:13].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.ClCCl.C(OC(C)C)(C)C>N1C=CC=CC=1>[CH3:11][C:8]1([CH3:10])[CH2:7][C:6]2[C:12]([CH3:13])=[C:2]([NH:1][S:22]([C:19]3[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=3)(=[O:24])=[O:23])[C:3]([CH3:15])=[C:4]([CH3:14])[C:5]=2[O:9]1
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참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 100358625-Amino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuranHCID 22238436Dichloromethane diisopropylether

생성물 1

HCID 106422232,2,4,6,7-Pentamethyl-5-(p-toluenesulfonylamino)-2,3-dihydrobenzofuran수율 68.8%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
50 °C

실험 절차

5-Amino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran (2.00 g, 9.74 mmol) and p-toluenesulfonyl chloride (2.04 g, 10.7 mmol) were dissolved in pyridine (30 ml) and stirred at 50° C. for 1 hour. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in chloroform. The mixture was washed with 1N hydrochloric acid and saturated saline and dried and then the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (hexaneethyl acetate, 97:3). The crude crystals were recrystallized from dichloromethane-isopropyl ether to obtain the desired compound (2.41 g, yield: 68.8% yield), m.p. 219°-220° C. (dichloromethane-isopropyl ether).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe mixture was washed with 1N hydrochloric acid and saturated saline
  4. customdried
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexaneethyl acetate, 97:3)
  7. customThe crude crystals were recrystallized from dichloromethane-isopropyl ether

출처 및 근거

ORD 기록
ord-3880387ac2fe4b69b09798f43e707123
출처 데이터셋
uspto-grants-1995_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05478844

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