Potassium Iodide → HCID 178509721, compound

HRID 1675903Notes

Reaction equation

HRID 1675903 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(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[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

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 178509721HCID 178509721, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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-13e9603523b844dda400d222fcf02ba0
Source dataset
uspto-grants-2011_08
Patent number
US08003804B2

Reaction notes

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