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

HRID 349453Notes

Reaction equation

HRID 349453 reaction equation
[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

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 233813-BromobenzonitrileHCID 33557Sodium Azide

Product 1

HCID 40730565-(3-bromophenyl)-1H-1,2,3,4-tetrazoleYield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0c72c1f26486480381200c3164af2e29
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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