Sulfuric Acid → 2-(4-Bromophenyl)-1,3,4-oxadiazole

HRID 1865163

Reaktionsgleichung

Reaktionsgleichung von HRID 1865163
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:17](OC(OCC)OCC)C>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][CH:17]=[N:9][N:8]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 222194-BromobenzohydrazideHCID 31214Ethyl orthoformate

Produkt 1

HCID 7151202-(4-Bromophenyl)-1,3,4-oxadiazoleAusbeute 89,9 %

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

To a suspension of 4-bromobenzoic hydrazide (200 g) in industrial methylated spirit (700 ml) was added triethylorthoformate (309 ml), industrial methylated spirit (100 ml) and sulphuric acid (0.8 ml). The reaction mixture was heated to reflux for 1 hour. The reaction mixture was cooled to 0-5° C. and product crystallised. Product was isolated, washed and dried to yield 2-(4-bromophenyl)-1,3,4-oxadiazole (186.1 g, 89.9%). 400 MHz NMR Spectrum: (DMSOd6) 9.35 (s, 1H), 7.98 (d, 1H), 7.95 (d, 1H), 7.84 (d, 1H), 7.81 (d, 1H); Mass Spectrum MH+ 224.9663 (calc. using 79-Br) Found 224.9701.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. customproduct crystallised
  4. customProduct was isolated
  5. washwashed
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fee7d7fff28d4a59a7705338d0e3b656
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07626020B2

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