Tetrahydrofuran → 1-Diallylcarbamoyl-3-ethylsulphinyl-1,2,4-triazole

HRID 371574Notes

Reaction equation

HRID 371574 reaction equation
[CH2:1]([S:3]([C:5]1[N:9]=[CH:8][NH:7][N:6]=1)=[O:4])[CH3:2].[CH2:10]([N:13]([CH2:17][CH:18]=[CH2:19])[C:14](Cl)=[O:15])[CH:11]=[CH2:12].O1CCCC1>C(N(CC)CC)C>[CH2:10]([N:13]([CH2:17][CH:18]=[CH2:19])[C:14]([N:7]1[CH:8]=[N:9][C:5]([S:3]([CH2:1][CH3:2])=[O:4])=[N:6]1)=[O:15])[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 3449313Diallylcarbamyl chlorideHCID 178477619HCID 178477619, compound

Product 1

HCID 203550741-Diallylcarbamoyl-3-ethylsulphinyl-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 4.35 g. 3-ethylsulphinyl-1,2,4-triazole, 6.0 ml. diallylcarbamoyl chloride, 25 ml. dry tetrahydrofuran and 7.5 ml. dry triethylamine was refluxed under anhydrous conditions for 2 hours. The reaction mixture was filtered and the filtrate distilled under reduced pressure to remove solvent, giving a residual oil which solidified on cooling. This solid product was recrystallized from petroleum ether (b.p. 60° - 80° C.) to give 1-diallylcarbamoyl-3-ethylsulphinyl-1,2,4-triazole, m.p. 41° - 43° C. Elemental analysis satisfactory.

Workup

  1. additionA mixture of 4.35 g
  2. filtrationThe reaction mixture was filtered
  3. distillationthe filtrate distilled under reduced pressure
  4. customto remove solvent
  5. customgiving a residual oil which
  6. temperatureon cooling
  7. customThis solid product was recrystallized from petroleum ether (b.p. 60° - 80° C.)

Sources & evidence

ORD record
ord-c7ddf42cf62641999581a5ad3c765aab
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

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