Reaktion #569985

Reaktionsgleichung

(benzyloxythiocarbonyl)hydrazine

sodium hydroxide

cyanogen bromide

→

5-amino-2-benzyloxy-1,3,4-thiadiazole

Ausbeute 58.5%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 250 ml round-bottom flask equipped with a mechanical stirrer
2. 2
   Sonstigebetween about 0°-5° C
3. 3
   SonstigeA precipitate formed
4. 4
   workup.ADDITIONWhen the addition
5. 5
   Filtrationthe reaction mixture was filtered
6. 6
   Waschenthe residue was rinsed well with water
7. 7
   Sonstigedried in vacuo
8. 8
   SonstigeThe product was recrystallized from methanol/water
9. 9
   Sonstigeto give a white solid of 16.6 g, 58.5% yield with a m.p. of 173°-175° C.

Vorschrift

In a 250 ml round-bottom flask equipped with a mechanical stirrer were mixed (benzyloxythiocarbonyl)hydrazine and 2N sodium hydroxide (90 ml). This mixture was stirred vigorously and cooled to 0° C. A solution of cyanogen bromide (14.5 g, 0.137 mol) in methanol (60 ml) was added dropwise at a rate that kept the reaction temperature between about 0°-5° C. A precipitate formed. When the addition was complete, the reaction mixture was filtered and the residue was rinsed well with water and dried in vacuo. The product was recrystallized from methanol/water to give a white solid of 16.6 g, 58.5% yield with a m.p. of 173°-175° C.

Quelle