Dimethylcarbamoyl Chloride → 1-Dimethylcarbamoyl-3,5-dipyrazinyl-1,2,4-triazole

HRID 127705Notes

Reaction equation

HRID 127705 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)[NH:9][N:8]=1.[H-].[Na+].[CH3:20][N:21]([CH3:25])[C:22](Cl)=[O:23]>O1CCCC1>[CH3:20][N:21]([CH3:25])[C:22]([N:8]1[C:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)=[N:11][C:10]([C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)=[N:9]1)=[O:23]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 135247872-(5-pyrazin-2-yl-4H-1,2,4-triazol-3-yl)pyrazine

Product 1

HCID 202857801-Dimethylcarbamoyl-3,5-dipyrazinyl-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 2.25 g. (0.01 mole) of 3,5-dipyrazinyl-1,2,4-triazole in 200 ml. of tetrahydrofuran is added 57% sodium hydride (0.42 g., 0.01 mole). The reaction mixture is heated at reflux for one hour, cooled, and a solution of dimethylcarbamoyl chloride (1 gram, 0.01 mole) in 10 ml. of tetrahydrofuran is added dropwise. The reaction mixture is then refluxed four hours, cooled, filtered and concentrated to a solid. After recrystallization from benzene 1-dimethylcarbamoyl-3,5-dipyrazinyl-1,2,4-triazole is obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for one hour
  3. temperaturecooled
  4. temperatureThe reaction mixture is then refluxed four hours
  5. temperaturecooled
  6. filtrationfiltered
  7. concentrationconcentrated to a solid
  8. customAfter recrystallization from benzene 1-dimethylcarbamoyl-3,5-dipyrazinyl-1,2,4-triazole
  9. customis obtained

Sources & evidence

ORD record
ord-7be2847047c94ec7a029b16ccc417b3f
Source dataset
uspto-grants-1981_03
Patent number
US04256887

Reaction notes

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