3-Cyanophenol → 3-(2H-Tetrazol-5-yl)phenol

HRID 2081083Notes

Reaction equation

HRID 2081083 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+]>CN(C)C=O>[N:2]1[NH:10][N:11]=[N:12][C:1]=1[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 133943-CyanophenolHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 134557633-(2H-Tetrazol-5-yl)phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 3-cyanophenol (4.14 g, 34.75 mmol) (Aldrich), sodium azide (2.49 g, 38.23 mmol) (Aldrich) and ammonium chloride (2.05 g, 38.23 mmol) in N,N-dimethylformamide (30 mL) were heated to 160° C. for 18 hours. The reaction mixture was concentrated. The residue was purified by C18 column eluting with acetonitrile-water to give 3-(2H-tetrazol-5-yl)-phenol. (Yield 0.9 g, 16%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was purified by C18 column
  3. washeluting with acetonitrile-water

Sources & evidence

ORD record
ord-f19a0ca0dcbb41f98078a35c837fac3a
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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