1H-1,2,4-Triazole → 1-(dibenzo[b,d]furan-4-yl)-1H-1,2,4-triazole

Participants

Role	Name	HCID	Charge
Reactant	1H-1,2,4-Triazole	HCID 9257	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	4-Iododibenzofuran	HCID 458257	—
Reactant	1-N,2-N-dimethylcyclohexane-1,2-diamine	HCID 551074	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-(dibenzo[b,d]furan-4-yl)-1H-1,2,4-triazole	HCID 59859024	60%

Reaction Conditions

Temperature	140 °C

Reaction Steps

A mixture of 4-iododibenzo[b,d]furan (5 g, 17.00 mmol), 1H-1,2,4-triazole (3.52 g, 51.0 mmol), CuI (0.162 g, 0.850 mmol), N1,N2-dimethylcyclohexane-1,2-diamine (0.537 mL, 3.40 mmol) and K3PO4 (7.58 g, 35.7 mmol) in DMF (50 mL) was heated at 140° C. for 48 h. After cooling to room temperature, the reaction mixture was filtered through a short plug of Celite®, and the solid was washed with DCM. The combined filtrate was evaporated and purified by column chromatography on silica gel with DCM as eluent to yield 1-(dibenzo[b,d]furan-4-yl)-1H-1,2,4-triazole (2.4 g, 60%) as white powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08692241B1
Source dataset	uspto-grants-2014_04
ORD ID	ord-73325ad428cb4a57be647ddc4f96d8a5
Source note	uspto-grants-2014_04