Dimethylformamide → (5-Phenyl-2H-tetrazol-2-yl)acetonitrile

HRID 2100249

Reaction equation

HRID 2100249 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:13][C:14]#[N:15].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]1([C:7]2[N:8]=[N:9][N:10]([CH2:13][C:14]#[N:15])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 178418369HCID 178418369, compound

Product 1

HCID 14415260(5-Phenyl-2H-tetrazol-2-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 146 mg (1 mmol) of 5-phenyltetrazole and 75 mg (1 mmol) of chloroacetonitrile was added three mL of dimethyl formamide. The resulting solution was stirred, then 158 mg (1 mmol) of potassium carbonate was added and the mixture was further stirred at room temperature for 18 hours. Twenty-five mL of water was then added and the mixture was extracted twice with 25 mL of ethyl acetate. Evaporation of the extracts left the crude product, which was purified by silica gel chromatography, leaving an oil that was pure by NMR.

Workup

  1. stirringthe mixture was further stirred at room temperature for 18 hours
  2. extractionthe mixture was extracted twice with 25 mL of ethyl acetate
  3. customEvaporation of the extracts
  4. waitleft the crude product, which
  5. customwas purified by silica gel chromatography
  6. customleaving an oil that

Sources & evidence

ORD record
ord-db064083d45f491e96cefddce65261cf
Source dataset
uspto-grants-2009_08
Patent number
US07572753B2

Linked notes

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