Methanesulfonic Acid → 2-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole

HRID 30641

Reaktionsgleichung

Reaktionsgleichung von HRID 30641
[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].[C:15](OC)(OC)(OC)[CH2:16][CH2:17][CH3:18].CS(O)(=O)=O.O1CCCC1>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[O:12][C:15]([CH2:16][CH2:17][CH3:18])=[N:14][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 6395Methanesulfonic AcidHCID 8028TetrahydrofuranHCID 1235121,1,1-TrimethoxybutaneHCID 2873312-(4-Nitrophenyl)acetohydrazide

Produkt 1

HCID 692088952-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-nitrophenyl)acetohydrazide (7.0 g), trimethyl orthobutyrate (16.01 g), methanesulfonic acid (0.69 g) and tetrahydrofuran (200 mL) was heated under reflux for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer 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)-5-propyl-1,3,4-oxadiazole was obtained as a colorless oil (7.73 g, yield 87%) from a fraction eluted with hexane-ethyl acetate (3:2-1:2, v/v).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d3f0feac829549ef83af5f08dda06d3d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423159B2

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