HCID 173550704, compound → HCID 12752145, compound

HRID 705019Notes

Reaction equation

HRID 705019 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:16]/[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)/[CH:7]=[N:8]NC1C=CC=CC=1>O.O1CCOCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[N:8][N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:16]=1

Participants

4

Reactant 1

HCID 173550704HCID 173550704, compound

Product 1

HCID 12752145HCID 12752145, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

An aqueous solution of hydrated copper sulphate (421 mg, 1.68 mmol) in 2 mL of demineralized water was added portion-wise to a solution of (2E)-2,2′-(1-(furan-2-yl)ethane-1,2-diylidene)bis(1-phenylhydrazine) (150 mg, 0.493 mmol) in dioxane (3.3 ml) while heating under reflux. After complete addition, heating was continued further for 2 hours. The solvent was then evaporated to dryness. The resulting crude material was subjected to flash column chromatography using an ethyl acetate/hexane solvent system (1-1.5%) to yield the desired compound 4-(furan-2-yl)-2-phenyl-2H-1,2,3-triazole as a yellow solid (60 mg, 57.7%). The HPLC purity of the final product was 96.03%. LC-MS [M+1] (C12H9N3O+H expected 212.07). The melting point of the final compound was observed to be 80° C. The 1H-NMR spectra was in accordance with the chemical structure.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. additionAfter complete addition
  4. temperatureheating
  5. customThe solvent was then evaporated to dryness

Sources & evidence

ORD record
ord-bfc4bfa4da534542bf1ad45ec822b58e
Source dataset
uspto-grants-2015_11
Patent number
US09173401B2

Reaction notes

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