Triethylamine hydrochloride → HCID 22723466, compound

HRID 1272202Notes

Reaction equation

HRID 1272202 reaction equation
C([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#N.Cl.C([N:13]([CH2:16]C)CC)C.[N-:18]=[N+:19]=[N-:20].[Na+]>C1(C)C=CC=CC=1>[N:13]1[CH:16]=[N:20][N:19]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[OH:9])[N:18]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 119072-HydroxybenzonitrileHCID 33557Sodium Azide

Product 1

HCID 22723466HCID 22723466, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A slurry of 2-cyano phenol (25 g, 209.87 mmol), triethylamine hydrochloride (43.3 g, 314.81 mmol), and sodium azide (20.5 g, 314.81 mmol) in toluene (200 mL) is heated to the reflux temperature of the mixture and then the mixture is allowed to stir at reflux for 15 hours. The mixture is cooled and washed with water (200 mL). The aqueous layer is washed with ether (100 mL), made acidic with concentrated HCl, and the resulting solid is collected by filtration. The solid is washed twice with water (200 mL) and dried under vacuum at 100° C. for 15 hours to give 33.05 g of 2-(tetrazol-3-yl)phenol (97%).

Workup

  1. temperatureat reflux for 15 hours
  2. temperatureThe mixture is cooled
  3. washwashed with water (200 mL)
  4. washThe aqueous layer is washed with ether (100 mL)
  5. filtrationthe resulting solid is collected by filtration
  6. washThe solid is washed twice with water (200 mL)
  7. customdried under vacuum at 100° C. for 15 hours

Sources & evidence

ORD record
ord-4ef741a3b4b6475aa1e50b345b451459
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

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