Dimethylformamide → 4,4'-(1-Benzyl-1H-1,2,4-triazole-3,5-diyl)dipyridine

HRID 1287496Notes

Reaction equation

HRID 1287496 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](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>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)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 24434994-(3-pyridin-4-yl-1H-1,2,4-triazol-5-yl)pyridine

Product 1

HCID 203168454,4'-(1-Benzyl-1H-1,2,4-triazole-3,5-diyl)dipyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3,5-bis(4-pyridyl)-1,2,4-triazole (4.4 g., 0.02 mol) in dry tetrahydrofuran (200 ml.) is added 57% sodium hydride in mineral oil (1 g., 0.024 mol.) and the mixture is heated 45 minutes at reflux. The suspension is concentrated to a solid, N,N-dimethylformamide (70 ml.) and benzyl chloride (2.8 g., 0.022 mol.) are added. The mixture is stirred 0.5 hour at ambient temperature followed by 4 hours at steam bath temperature. The solution is concentrated to a gum, water is added and the material solidifies. After recrystallization from methylcyclohexane 1.4 g. of 1-benzyl-3,5-bis(4-pyridyl)-1,2,4-triazole, melting at 136°-138°C. is obtained.

Workup

  1. temperaturethe mixture is heated 45 minutes
  2. temperatureat reflux
  3. additionare added
  4. waitfollowed by 4 hours at steam bath
  5. concentrationThe solution is concentrated to a gum, water
  6. additionis added
  7. customAfter recrystallization from methylcyclohexane 1.4 g

Sources & evidence

ORD record
ord-7ca4fda9f93e40749f4ce33aa574ccf6
Source dataset
uspto-grants-1976_10
Patent number
US03984558

Reaction notes

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