Phenylhydrazine → HCID 173550704, compound

HRID 705018Notes

Reaction equation

HRID 705018 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH:8]1OC2C(Cl)=C(Cl)C(Cl)=C(Cl)C=2O1)=O.[C:21]1([NH:27][NH2:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:28]/[NH:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)/[CH:8]=[N:28][NH:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 12752103HCID 12752103, compound

Product 1

HCID 173550704HCID 173550704, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customDuring the course of the reflux, a yellow solid initially precipitated
  4. dissolutiondissolved upon further heating
  5. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-f6d1e38c78bc4f2b8f8cb27ad416cea5
Source dataset
uspto-grants-2015_11
Patent number
US09173401B2

Reaction notes

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