Acetic Acid → 1-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbonitrile

HRID 839219Notes

Reaction equation

HRID 839219 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14]#[N:15])=[CH:12][NH:11][N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].CI.[C:20](O)(=O)C>CN(C)C=O.O>[CH3:20][N:11]1[CH:12]=[C:13]([C:14]#[N:15])[C:9]([C:7]2[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:10]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1785104403-(5-nitro-2-furyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 203260431-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbonitrileYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Add 15.4 g of 3-(5-nitro-2-furyl)-1H-pyrazole-4-carbonitrile portionwise to a suspension of 2.5 g of sodium hydride (80% in liquid paraffin) in 90 ml of dimethylformamide while stirring and under nitrogen at from -2° C to -5° C. Stir the thus-obtained reaction mixture for 30 minutes and then add dropwise thereto a solution of 11.8 g of methyl iodide in 20 ml of dimethylformamide. After stirring for 30 minutes, admix therewith 0.6 g of glacial acetic acid and stir the resulting solution into 220 g of ice and water. Remove formed precipitate by vacuum filtration and recrystallize residue twice from dimethylformamide and water. Dry the residue in vacuo. Recrystallize the resulting 13.5 g of product three more times from dimethylformamide and water to obtain a 57% yield of 1-methyl-3-(5-nitro-2-furyl)pyrazole-4-carbonitrile [m.p. 176.5° to 177.5° C].

Workup

  1. stirringStir
  2. customthe thus-obtained reaction mixture for 30 minutes
  3. additionadd dropwise
  4. stirringAfter stirring for 30 minutes
  5. customRemove
  6. customformed precipitate
  7. filtrationby vacuum filtration
  8. customrecrystallize residue twice from dimethylformamide and water
  9. customDry the residue in vacuo
  10. customRecrystallize the resulting 13.5 g of product three more times from dimethylformamide and water

Sources & evidence

ORD record
ord-f9287ec750a7468bb14e4d5c08189f6d
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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