1H-1,2,4-Triazole → 1H-1,2,4-Triazole, 1-phenyl-

HRID 1243078Notes

Reaction equation

HRID 1243078 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.I[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.CCCCCC.C(OCC)(=O)C.CN(C)C=O>[C:7]1([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 834321H-1,2,4-Triazole, 1-phenyl-Yield 93%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using the general procedure, 1,2,4-triazole (0.069 g, 1.00 mmol) was coupled with iodobenzene (134 μL, 1.20 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %) and dimethylformamide (1.0 mL) to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 3:1) provided 0.135 g (93% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.58 (s, 1H), 8.10 (s, 1H), 7.66 (m, 2H), 7.47 (m, 2H), 7.37 (m, 1H).

Workup

  1. customto give the crude product

Sources & evidence

ORD record
ord-dd95dde221434396aa978e519c071edf
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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