Triethylamine hydrochloride → 5-(3-bromophenyl)-1H-1,2,3,4-tetrazole

HRID 349453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349453
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Cl.C(N(CC)CC)C.[N-:18]=[N+:19]=[N-:20].[Na+]>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[N:18]=[N:19][NH:20][N:6]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 11130Triethylamine hydrochlorideHCID 233813-BromobenzonitrileHCID 33557Sodium Azide

Produkt 1

HCID 40730565-(3-bromophenyl)-1H-1,2,3,4-tetrazoleAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 3-bromobenzonitrile (30.00 g, 164.8 mmol) in toluene (300 mL) was treated with triethylamine hydrochloride (68.05 g, 494.4 mmol) and sodium azide (32.14 g, 494.4 mmol) and the reaction mixture heated to reflux over night. Cooled to room temperature, diluted with water (300 mL), the layers were separated, and the aqueous portion acidified to pH 1 using concentrated HCl. The precipitated solid was collected by filtration, washed with water, and dried to give 34.96 g of product (94.3% yield).

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux over night
  3. customthe layers were separated
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0c72c1f26486480381200c3164af2e29
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179822B2

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