1,2-Dibromoethane → 1-(1-methyl-1H-1,2,4-triazol-5-yl)cyclopropanecarbonitrile

HRID 931168Notes

Reaction equation

HRID 931168 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([CH2:9][C:10]#[N:11])=[N:7][CH:6]=[N:5]1.Br[CH2:13][CH2:14]Br>CS(C)=O>[CH3:3][N:4]1[C:8]([C:9]2([C:10]#[N:11])[CH2:14][CH2:13]2)=[N:7][CH:6]=[N:5]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydride2×HCID 656015352-(1-methyl-1H-1,2,4-triazol-5-yl)acetonitrile

Product 1

HCID 898542431-(1-methyl-1H-1,2,4-triazol-5-yl)cyclopropanecarbonitrileYield 64.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil, 1.06 g, 44.2 mmol) was washed twice with petroleum ether under nitrogen. Then dimethylsulfoxide (10 mL) was added at room temperature. A solution of 2-(1-methyl-1H-1,2,4-triazol-5-yl)acetonitrile (0.9 g, 7.36 mmol) and 1,2-dibromoethane (4.147 g, 22.1 mmol) in dimethylsulfoxide (20 mL) was added dropwise to the sodium hydride suspension over a period of 20 min. The reaction mixture was stirred at room temperature for 3 h. The mixture was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 5-15% ethyl acetate in petroleum ether) to afford 1-(1-methyl-1H-1,2,4-triazol-5-yl)cyclopropanecarbonitrile (0.7 g) as a colorless oil.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified via column chromatography (100-200 mesh silica gel, 5-15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d8f5c32deb4b491f97b0ae00d2b4a4f3
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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