Sodium Azide → 4-(Azidomethyl)benzonitrile

HRID 482255

Reaktionsgleichung

Reaktionsgleichung von HRID 482255
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=1)#[N:6]>O.CN(C=O)C.C1(C)C=CC=CC=1>[C:5]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11][N:1]=[N+:2]=[N-:3])=[CH:9][CH:8]=1)#[N:6]

Komponenten

6

Edukt 2

HCID 33557Sodium AzideHCID 869964-(Bromomethyl)benzonitrile

Produkt 1

HCID 110736914-(Azidomethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 20.23 g (0.31 mol) sodium azide in 50 ml water was added to 49.15 g (251 mmol) 4-cyanobenzyl bromide in 200 ml DMF at ambient temperature. An exothermic reaction took place and after 1.5 h the reaction mixture was diluted with 200 ml toluene(caution: In order to avoid separation of potentially explosive azide compounds it is adviseable to add the toluene to the reaction mixture before addition of the water) and 500 ml water. The aqueous phase was extracted with an additional 2×50 ml toluene. The combined organic extracts were washed with 2×50 ml water and brine and finally dried (MgSO4) and filtered.

Aufarbeitung

  1. customAn exothermic reaction
  2. customseparation of potentially explosive azide compounds it
  3. additionto add the toluene to the reaction mixture
  4. additionbefore addition of the water) and 500 ml water
  5. extractionThe aqueous phase was extracted with an additional 2×50 ml toluene
  6. washThe combined organic extracts were washed with 2×50 ml water and brine
  7. dry with materialfinally dried (MgSO4)
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-3b035c5056d5497c99024978f4761643
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795896

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