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Sodium Hydroxide → 5-[4-(benzyloxy)phenyl]-2H-tetrazole

HRID 423254
Notes
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Reaction equation

HRID 423254 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:17]=[N+:18]=[N-:19].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[N:17]=[N:18][NH:19][N:14]=2)=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 5613714-Benzyloxybenzonitrile

Product 1

HCID 47709095-[4-(benzyloxy)phenyl]-2H-tetrazoleYield 95%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-benzyloxybenzonitrile (2.0 g) in dimethylformamide (15 mL) were added sodium azide (932 mg) and ammonium chloride (767 mg). The mixture was stirred at 110° C. overnight under heating and then allowed to stand for cooling to room temperature. 1N aqueous sodium hydroxide was added thereto to adjust the pH to about 10, followed by washing with diethyl ether. To the aqueous layer was added 1N hydrochloric acid, and the resulting precipitated solid was filtered to give the title compound (2.29 g).

Workup

  1. temperatureunder heating
  2. temperaturefor cooling to room temperature
  3. washby washing with diethyl ether
  4. additionTo the aqueous layer was added 1N hydrochloric acid
  5. customthe resulting precipitated solid
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-aa7d65929a8b4b7f87d2782eda47a500
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08101774B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes