Potassium Iodide → 3,5-dibromo-1-(4-methoxybenzyl)-1H-1,2,4-triazole

HRID 1054944Notes

Reaction equation

HRID 1054944 reaction equation
[Br:1][C:2]1[N:6]=[C:5]([Br:7])[NH:4][N:3]=1.[I-].[K+].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Br:1][C:2]1[N:6]=[C:5]([Br:7])[N:4]([CH2:16][C:15]2[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[N:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 699934-Methyloxybenzyl chlorideHCID 81531DiisopropylethylamineHCID 819043,5-Dibromo-4H-1,2,4-triazole

Product 1

HCID 179319143,5-dibromo-1-(4-methoxybenzyl)-1H-1,2,4-triazoleYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,5-dibromo-1H-1,2,4-triazole (1.5 g, 6.61 mmol, Eq: 1.00), potassium iodide (110 mg, 661 μmol, Eq: 0.10), 4-methoxybenzyl chloride (1.14 g, 990 μl, 7.27 mmol, Eq: 1.1) and N,N-diisopropylethylamine (1.71 g, 2.31 ml, 13.2 mmol, Eq: 2.0) was stirred in acetonitrile (23.0 ml) overnight at room temperature. The crude material was applied on silica gel and purified by column chromatography using heptane/ethyl acetate gradient as eluent to afford 3,5-dibromo-1-(4-methoxy-benzyl)-1H-[1,2,4]triazole (1.79 g/78.0%) as a white solid. MS: m/e=345685051 (M+H+), mp: 75.7° C.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-3e56d48fd2234805b864d6ca6fef15e3
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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