2-Bromobenzonitrile → 5-(2-Bromophenyl)-1H-tetrazole

HRID 1440452Notes

Reaction equation

HRID 1440452 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]1[NH:12][N:11]=[N:10][N:5]=1

Participants

5

Reactant 3

HCID 162722-BromobenzonitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 1784193735-(2-Bromophenyl)-1H-tetrazoleYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromobenzonitrile (10.0 g, 0.055 mol), sodium azide (3.9 g, 0.060 mol), ammonium chloride (3.2 g, 0.060 mol), and DMF (90 mL) was heated at 100° C. for 18 h. The mixture was concentrated, taken up in water, and made basic (pH 9) with 1N KOH. The aqueous mixture was extracted with ether (discarded) and acidified with 2N HCl. The precipitate was collected by filtration to give 9.1 g (73%) of product as an off-white solid, mp 179°-181° C.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionThe aqueous mixture was extracted with ether (discarded)
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2ccfa16cc54f465eb2e4e308e1eb2c4a
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

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