Diethylcarbamoyl chloride → 1-Diethylcarbamoyl-3-propylsulphinyl-1,2,4-triazole

HRID 371588Notes

Reaction equation

HRID 371588 reaction equation
[CH2:1]([S:4]([C:6]1[N:10]=[CH:9][NH:8][N:7]=1)=[O:5])[CH2:2][CH3:3].[CH2:11]([N:13]([CH2:17][CH3:18])[C:14](Cl)=[O:15])[CH3:12].O1CCCC1>C(N(CC)CC)C>[CH2:11]([N:13]([CH2:17][CH3:18])[C:14]([N:8]1[CH:9]=[N:10][C:6]([S:4]([CH2:1][CH2:2][CH3:3])=[O:5])=[N:7]1)=[O:15])[CH3:12]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 8028TetrahydrofuranHCID 1784610023-Propylsulphinyl-1,2,4-triazole

Product 1

HCID 201633711-Diethylcarbamoyl-3-propylsulphinyl-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 4.8 g. 3-propylsulphinyl-1,2,4-triazole, 4.48 g. diethylcarbamoyl chloride, 40 ml. dry tetrahydrofuran and 6 ml. dry triethylamine was refluxed under anhydrous conditions for 5 hours. The cooled reaction mixture was filtered to remove triethylamine hydrochloride. The filtrate was diluted with petroleum ether (b.p. 40° - 60° C.), causing the deposition of an oil which gradually solidified. The solid product was collected and recrystallized from a mixture of ether and petroleum ether (b.p. 40° - 60° C.) to give 1-diethylcarbamoyl-3-propylsulphinyl-1,2,4-triazole, m.p. 50.5° - 51.5° C.

Workup

  1. additionA mixture of 4.8 g
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customto remove triethylamine hydrochloride
  5. additionThe filtrate was diluted with petroleum ether (b.p. 40° - 60° C.)
  6. customThe solid product was collected
  7. customrecrystallized from a mixture of ether and petroleum ether (b.p. 40° - 60° C.)

Sources & evidence

ORD record
ord-fa7958c738b740d6adf0d979da26cedf
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

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