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

HRID 234258
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 234258
[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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Komponenten

5

Edukt 3

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

Produkt 1

HCID 106422232,2,4,6,7-Pentamethyl-5-(p-toluenesulfonylamino)-2,3-dihydrobenzofuranAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049
Pyridine
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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 in 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 (hexane-ethyl 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).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe mixture was washed with in 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 (hexane-ethyl acetate, 97:3)
  7. customThe crude crystals were recrystallized from dichloromethane-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0e3ce6ce35684d96a973d22b98f62e0a
Quelldatensatz
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05594154

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