Sulfuric Acid → N-[2-(2-Methyl-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]acetamide

HRID 883227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883227
[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12](=[CH:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 67354710N-[2-(2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)ethyl]acetamide

Produkt 1

HCID 23725512N-[2-(2-Methyl-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]acetamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

N-[2-(2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)ethyl]acetamide (63.5 mg, 0.248 mmol) was dissolved in toluene (2.5 mL), sulfuric acid (24.3 μL, 0.248 mmol) was added, and the mixture was stirred at 100° C. for 5 hr. To the reaction solution was added saturated aqueous sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10) to give the title compound (40.0 mg, yield 63%).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10)

Quellen und Nachweise

ORD-Eintrag
ord-7d5793dac27049c294e2b61473cac1d1
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236837B2

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