1H-1,2,4-Triazole → HCID 178509721, compound

HRID 1198169Notes

Reaction equation

HRID 1198169 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].[H][H].Br[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1>CN(C)C=O.O>[NH:1]1[CH:5]=[N:4][C:3]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)=[N:2]1

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 178509721HCID 178509721, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

23.5 g of 1,2,4-triazole is combined under cooling in 250 ml of N,N-dimethylformamide in incremental portions with 14.15 g of sodium hydride, 60% in oil, and stirred at 25° for 1 hour until hydrogen release has ceased. To this solution is added 50 g of 4-(bromomethyl)benzonitrile in two portions under ice cooling at 5°, and the mixture is stirred for 2 hours at 25°. For working up purposes, 200 ml of water is added under ice cooling, the mixture is stirred for 1 hour, extracted with ethyl acetate, washed neutral with water, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with dichloromethane/methanol, yielding 31.73 g of 4-[1-(1,2,4-triazolyl)methyl]benzonitrile as colorless crystals, mp. 72°-73°.

Workup

  1. additionis added under ice cooling
  2. stirringthe mixture is stirred for 1 hour
  3. extractionextracted with ethyl acetate
  4. washwashed neutral with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness under vacuum
  7. customchromatographed on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-07c5fcd901f244faa0052dd8bedf0971
Source dataset
uspto-grants-1994_01
Patent number
US05280035

Reaction notes

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