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

HRID 1606065Notes

Reaction equation

HRID 1606065 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. EXAMPLE 19

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-6720ec3f750a4b28b9eaac6d58f28bbd
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

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