Dimethylformamide → HCID 20309755, compound

HRID 1763274Notes

Reaction equation

HRID 1763274 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[NH:9][N:8]=2)=[CH:3][CH:2]=1.[H-].[Na+].CN(C)C=O.[CH2:25](I)[CH2:26][CH3:27]>O1CCCC1>[CH2:25]([N:8]1[C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[N:11][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:9]1)[CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 24434994-(3-pyridin-4-yl-1H-1,2,4-triazol-5-yl)pyridine

Product 1

HCID 20309755HCID 20309755, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3,5-bis(4-pyridyl)-1,2,4-triazole (4.4 g., 0.02 mole) in dry tetrahydrofuran (200 ml.) is added 57% sodium hydride in mineral oil (1 g. 0.024 mole) and the mixture is heated 45 minutes at reflux. The suspension is concentrated to a solid, N,N-dimethylformamide (70 ml.) and n-propyl iodide (0.022 mole) are added. The mixture is stirred 0.5 hour at ambient temperature followed by heating on the steam bath for 4 hours. The solution is concentrated to a gum, water is added and the material solidifies. Following recrystallization from methylcyclohexane there is obtained 1-n-propyl-3,5-bis(4-pyridyl)-1,2,4-triazole, m.p. 88°-89.5° C.

Workup

  1. temperaturethe mixture is heated 45 minutes
  2. temperatureat reflux
  3. additionare added
  4. temperatureby heating on the steam bath for 4 hours
  5. concentrationThe solution is concentrated to a gum, water
  6. additionis added
  7. customrecrystallization from methylcyclohexane

Sources & evidence

ORD record
ord-900006022ce04449b7216bd71130ed5f
Source dataset
uspto-grants-1978_09
Patent number
US04111944

Reaction notes

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