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

HRID 35912

Reaktionsgleichung

Reaktionsgleichung von HRID 35912
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 178509721HCID 178509721, VerbindungAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8d6520500afa40f5a0104b2c21c63885
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411982

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