1H-1,2,4-Triazole → 4-((4H-1,2,4-Triazol-4-yl)methyl)benzonitrile

HRID 1675904Notes

Reaction equation

HRID 1675904 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1>C(Cl)(Cl)Cl.C(#N)C>[NH:11]1[CH:15]=[N:14][C:13]([CH2:2][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)=[N:12]1.[N:11]1[N:12]=[CH:13][N:14]([CH2:2][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)[CH:15]=1

Participants

6

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 869964-(Bromomethyl)benzonitrile

Product 2

HCID 150297504-((4H-1,2,4-Triazol-4-yl)methyl)benzonitrileHCID 178509721HCID 178509721, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

In the process described in '672, the reaction of refluxing 4-bromomethyl benzonitrile with 1,2,4-triazole in the presence of potassium carbonate and potassium iodide in acetone solvent (according to example 24) gives 4-[1-(1,2,4-triazolyl)methyl]benzonitrile of the formula II in an amount of 87 wt %, and 4-[4-(1,2,4-triazol-4-yl)methyl]benzonitrile of the formula III in an amount of 11 wt %, along with 2% of other impurities. The reaction of 4-bromomethyl benzonitrile with 1,2,4-triazole in a mixture of chloroform and acetonitrile (example 9) gives 4-[1-(1,2,4-triazolyl)methyl]benzonitrile of the formula II in an amount of 30 wt %, and 4-[(1,2,4-triazol-4-yl)methyl]benzonitrile of the formula III in an amount of 40 wt %, along with 20 wt % other impurities. The ratios of intended product to impurity for the prior art processes have been determined by experiment.

Sources & evidence

ORD record
ord-f9837639b325415487f2701c06364465
Source dataset
uspto-grants-2011_08
Patent number
US08003804B2

Reaction notes

Loading…