Dimethyl Sulfoxide → Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-

HRID 1488489Notes

Reaction equation

HRID 1488489 reaction equation
[NH2:1][N:2]1[CH:6]=[N:5][N:4]=[CH:3]1.CS(C)=O.[H-].[Na+].F[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1>O>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([NH:1][N:2]2[CH:6]=[N:5][N:4]=[CH:3]2)=[CH:15][CH:16]=1)#[N:19]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 114324-Amino-1,2,4-triazoleHCID 145174-FluorobenzonitrileHCID 24758Sodium hydride

Product 1

HCID 10307909Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.52 Grams of 4-amino-1,2,4-triazole was added little by little to a dimethylsulfoxide suspension of 1.2 g of sodium hydride at room temperature. After stirred for 3 hours at room temperature, 1.21 g of 4-fluorobenzonitrile was added thereto all at a time, and stirring was continued for further one hour. Water was added to the reaction solution, and the mixture was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The crystals obtained were washed with ethyl acetate to give 1.09 g of 4-[(4-cyanophenyl)amino]-4H-1,2,4-triazole.

Workup

  1. stirringall at a time, and stirring
  2. waitwas continued for further one hour
  3. extractionthe mixture was then extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe crystals obtained
  7. washwere washed with ethyl acetate

Sources & evidence

ORD record
ord-253a5a2164e04a6cbc02deeeb05ee9e2
Source dataset
uspto-grants-1997_10
Patent number
US05674886

Reaction notes

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