Methanol → HCID 13655520, compound

HRID 1380785Notes

Reaction equation

HRID 1380785 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C[O-].[Na+].CO.Cl[CH:12]([CH3:15])[C:13]#[N:14]>CN(C)C=O>[C:13]([CH:12]([N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)[CH3:15])#[N:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 92571H-1,2,4-TriazoleHCID 5192252-ChloropropionitrileHCID 10942334Sodium Methoxide

Product 1

HCID 13655520HCID 13655520, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

In this example, a mixture containing 13.47 gms (0.195 mole) of 1,2,4-triazole and 10.53 gms (0.195 mole) of sodium methoxide in 200 mls of dimethylforamide was refluxed until no further evolution of the methanol by-product was observed. The reaction mixture was then cooled to 0° C. and then 19.23 gms of 2-chloropropionitrile dissolved in 25 mls of dimethylforamide were added dropwise with stirring. The mixture was then stirred overnight (about 12 to 14 hours) at room temperature and then filtered. The dimethylforamide was then removed by vacuum evaporation. The residue was dissolved in methylene chloride and filtered through neutralized silica gel. The filtrate was evaporated affording 16.73 gms of the title compound as a brown liquid.

Workup

  1. additionwere added dropwise
  2. stirringThe mixture was then stirred overnight (about 12 to 14 hours) at room temperature
  3. filtrationfiltered
  4. customThe dimethylforamide was then removed by vacuum evaporation
  5. dissolutionThe residue was dissolved in methylene chloride
  6. filtrationfiltered through neutralized silica gel
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-70f9893f39eb44c4b2aba9cb1a253b67
Source dataset
uspto-grants-1986_04
Patent number
US04584008

Reaction notes

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