Water → 4-[1,2,4]Triazol-1-yl-nicotinonitrile

HRID 1171065Notes

Reaction equation

HRID 1171065 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[NH:10]1[CH:14]=[N:13][CH:12]=[N:11]1.O>CS(C)=O>[N:10]1([C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=2)[CH:14]=[N:13][CH:12]=[N:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 134111124-Chloro-nicotinonitrile

Product 1

HCID 687668474-[1,2,4]Triazol-1-yl-nicotinonitrileYield 82.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of known 4-chloro-nicotinonitrile (3.325 g, 24 mmol) (Tetrahedron Lett. 46:135-137, 2005), 1H-[1,2,4]triazole (1.99 g, 28.8 mmol), and CsCO3 (9.30 g, 28.5 mmol) in DMSO (5.0 mL) was stirred at 55° C. for 1.5 h. The resulting thin light brown slurry was shaken with water (50 mL) and extracted with DCM (1×50 mL, 2×25 mL). The organic layers were combined, dried (Na2SO4), and concentrated under vacuum at 90° C. to afford the title compound as a beige solid (3.38 g, 82%).

Workup

  1. extractionextracted with DCM (1×50 mL, 2×25 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under vacuum at 90° C.

Sources & evidence

ORD record
ord-7952713e048d4f00a163207b97e27809
Source dataset
uspto-grants-2010_11
Patent number
US07829584B2

Reaction notes

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