Hydrochloric Acid → 3-(2H-tetrazol-5-yl)-2-(trifluoromethyl)pyridine

HRID 62015Notes

Reaction equation

HRID 62015 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[N:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[N-:13]=[N+:14]=[N-:15].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[N:6]1[NH:13][N:14]=[N:15][C:5]=1[C:4]1[C:3]([C:2]([F:11])([F:1])[F:12])=[N:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 269863872-(Trifluoromethyl)pyridine-3-carbonitrile

Product 1

HCID 687044913-(2H-tetrazol-5-yl)-2-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-(trifluoromethyl)nicotinonitrile (0.43 g, 2.50 mmol), sodium azide (0.24 g, 3.75 mmol), and ammonium chloride (0.20 g, 3.75 mmol) in dimethylformamide (2.5 mL) was stirred at 85° C. for 20 hours. After cooling to room temperature, the reaction mixture was poured onto water (20 mL) and acidified with dilute hydrochloric acid. The resulting precipitate was collected, washed with water and dried to yield 3-(2H-tetrazol-5-yl)-2-(trifluoromethyl)pyridine, 0.484 g (90%).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe reaction mixture was poured onto water (20 mL)
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7bdffca34e2d4750a24299441ea112f8
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Reaction notes

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