Methanesulfonic Acid → HCID 69210542, Verbindung

HRID 30640

Reaktionsgleichung

Reaktionsgleichung von HRID 30640
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:15](OCC)(OCC)OCC.CS(O)(=O)=O.O1CCCC1>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[O:12][CH:15]=[N:14][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 6395Methanesulfonic AcidHCID 8028TetrahydrofuranHCID 31214Ethyl orthoformateHCID 2873312-(4-Nitrophenyl)acetohydrazide

Produkt 1

HCID 69210542HCID 69210542, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-nitrophenyl)acetohydrazide (2.50 g), triethyl orthoformate (5.69 g), methanesulfonic acid (0.25 g) and tetrahydrofuran (50 mL) was heated under reflux for 1 hr. The reaction mixture was diluted with ethyl acetate. The mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and 2-(4-nitrobenzyl)-1,3,4-oxadiazole was obtained as pale-yellow crystals (1.92 g, yield 73%) from a fraction eluted with hexane-ethyl acetate (3:1-1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 104-105° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. washThe mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-909822fc3a3a41b58f5c0c1e101a4a61
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423159B2

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