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

HRID 1834774Notes

Reaction equation

HRID 1834774 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 (.42 g., 0.01 mole). The reaction mixture is heated at reflux for 1 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 4 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 1 hour
  3. temperaturecooled
  4. temperatureThe reaction mixture is then refluxed 4 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-0533e6407fa94371af2fd5bacba57257
Source dataset
uspto-grants-1978_01
Patent number
US04071518

Reaction notes

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