4-Aminobenzonitrile → 4-(1H-tetrazol-5-yl)aniline

HRID 1361032Notes

Reaction equation

HRID 1361032 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2[N:10]=[N:11][NH:12][N:7]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 10792164-(1H-tetrazol-5-yl)aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 4-aminobenzonitrile (10 g, 84.6 mmol), sodium azide (16.5 g, 254 mmol) and ammonium chloride (13.6 g, 254 mmol) in DMF was heated at 125° C. for 16 hours. The cooled mixture was filtered and the filtrate was concentrated in vacuo. The residue was added water (200 mL) and diethyl ether (200 mL) which resulted in crystallisation. The mixture was filtered and the solid was dried in vacuo at 40° C. for 16 hours to afford 5-(4-aminophenyl)-2H-tetrazole.

Workup

  1. filtrationThe cooled mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was added water (200 mL) and diethyl ether (200 mL) which
  4. customresulted in crystallisation
  5. filtrationThe mixture was filtered
  6. customthe solid was dried in vacuo at 40° C. for 16 hours

Sources & evidence

ORD record
ord-6bf267942e8943dbb913b10e35ced7fb
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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