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

HRID 2364593

Reaction equation

HRID 2364593 reaction equation
I[C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH:15]1[CH:19]=[N:18][CH:17]=[N:16]1.CNC1CCCCC1NC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[CH:5]1[C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][C:7]=2[C:2]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 62657Potassium Phosphate, TribasicHCID 4582574-IododibenzofuranHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamine

Product 1

HCID 598590241-(dibenzo[b,d]furan-4-yl)-1H-1,2,4-triazoleYield 60%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

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.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through a short plug of Celite®
  3. washthe solid was washed with DCM
  4. customThe combined filtrate was evaporated
  5. custompurified by column chromatography on silica gel with DCM as eluent

Sources & evidence

ORD record
ord-73325ad428cb4a57be647ddc4f96d8a5
Source dataset
uspto-grants-2014_04
Patent number
US08692241B1

Linked notes

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