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Iodoacetamide → 2-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide

HRID 2095833
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2095833
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.I[CH2:38][C:39]([NH2:41])=[O:40].C(OCC)(=O)C>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12](=[N:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[N:13]([CH2:38][C:39]([NH2:41])=[O:40])[CH:14]=2)=[CH:26][CH:27]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 3727IodoacetamideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 66968540N-{5-[(4-methoxybenzyl)oxy]pyridin-2-yl}-4-methylbenzenesulfonamide

Produkt 1

HCID 669689682-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamideAusbeute 299,7 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of N-{5-[(4-methoxybenzyl)oxy]pyridin-2-yl}-4-methylbenzenesulfonamide (10.0 g, 26.0 mmol) in N,N-dimethylformamide (85 mL) were added N,N-diisopropylethylamine (6.8 mL, 39.0 mmol) and iodoacetamide (5.77 g, 31.0 mmol), and the mixture was stirred at 60° C. for 5 hr. After cooling to room temperature, ethyl acetate and water were added, and the mixture was extracted 3 times with a mixed solution of ethyl acetate and tetrahydrofuran. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (34.4 g, 75%) as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted 3 times with a mixed solution of ethyl acetate and tetrahydrofuran
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. washThe obtained residue was washed with ethyl acetate
  8. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-3fe98c128c754fca8861d1e50f5a6dc3
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08445509B2

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