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

HRID 371577Notes

Reaction equation

HRID 371577 reaction equation
[CH:1]([S:4]([C:6]1[N:10]=[CH:9][NH:8][N:7]=1)=[O:5])([CH3:3])[CH3:2].[CH2:11]([N:14]([CH2:18][CH:19]=[CH2:20])[C:15](Cl)=[O:16])[CH:12]=[CH2:13].O1CCCC1>C(N(CC)CC)C>[CH2:11]([N:14]([CH2:18][CH:19]=[CH2:20])[C:15]([N:8]1[CH:9]=[N:10][C:6]([S:4]([CH:1]([CH3:3])[CH3:2])=[O:5])=[N:7]1)=[O:16])[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 3449313Diallylcarbamyl chlorideHCID 1784610013-Isopropylsulphinyl-1,2,4-triazole

Product 1

HCID 203550491-Diallylcarbamoyl-3-isopropylsulphinyl-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 6.4 g. 3-isopropylsulphinyl-1,2,4-triazole, 8.0 ml. diallylcarbamoyl chloride, 25 ml. dry tetrahydrofuran and 10 ml. dry triethylamine was refluxed under anhydrous conditions for 2 hours. The cooled reaction mixture was filtered and the filtrate was distilled under reduced pressure to give an oily residue which subsequently solidified. This solid residue was recrystallized from petroleum ether (b.p. 60° - 80° C.) to give 1-diallylcarbamoyl-3-isopropylsulphinyl-1,2,4-triazole, m.p. 32° - 34° C. Elemental analysis satisfactory.

Workup

  1. additionA mixture of 6.4 g
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. distillationthe filtrate was distilled under reduced pressure
  5. customto give an oily residue which
  6. customThis solid residue was recrystallized from petroleum ether (b.p. 60° - 80° C.)

Sources & evidence

ORD record
ord-0ae279299cf94091a3ecb629d3ed6a15
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

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