Reaction #792200

Reaction equation

furan-2-yl(4,5,6,7-tetrachlorobenzo[d][1,3]dioxol-2-yl)methanone

phenylhydrazine

→

(2E)-2,2′-(1-(furan-2-yl)ethane-1,2-diylidene)bis(1-phenylhydrazine)

Yield 87.0%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for 30 minutes
3. 3
   OtherDuring the course of the reflux, a yellow solid initially precipitated
4. 4
   workup.DISSOLUTIONdissolved upon further heating
5. 5
   OtherThe solvent was evaporated to dryness

Procedure

A mixture of furan-2-yl(4,5,6,7-tetrachlorobenzo[d][1,3]dioxol-2-yl)methanone (200 mg, 0.568 mmol) and phenylhydrazine (185 mg, 1.704 mmol) in ethanol (3 ml) was heated under reflux for 30 minutes. During the course of the reflux, a yellow solid initially precipitated, but then dissolved upon further heating. The solvent was evaporated to dryness, and the resulting crude material was subjected to flash column chromatography using 7% ethyl acetate/hexane as an eluent to yield (2E)-2,2′-(1-(furan-2-yl)ethane-1,2-diylidene)bis(1-phenylhydrazine) as a yellow solid (150 mg, 87%).

Source