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

HRID 1606064Notes

Reaction equation

HRID 1606064 reaction equation
[CH2:1]([S:3]([C:6]1[N:10]=[CH:9][NH:8][N:7]=1)(=[O:5])=[O:4])[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:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[N:7]1)=[O:16])[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 3449313Diallylcarbamyl chlorideHCID 178477666HCID 178477666, compound

Product 1

HCID 203551341-Diallylcarbamoyl-3-ethylsulphonyl-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 6.45 g. 3-ethylsulphonyl-1,2,4-triazole, 6.6 g. diallylcarbamoyl chloride, 25 ml. dry tetrahydrofuran and 8 ml. dry triethylamine was refluxed under anhydrous conditions for 1.5 hours. The cooled reaction mixture was filtered and the filtrate distilled under reduced pressure to remove solvent and give a product which distilled at 187°C./0.2 mm. This product solidified and was recrystallized from petroleum ether (b.p. 60° - 80°C.) to give 1-diallylcarbamoyl-3-ethylsulphonyl-1,2,4-triazole, m.p. 39° - 42°C. Elemental analysis satisfactory.

Workup

  1. additionA mixture of 6.45 g
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. distillationthe filtrate distilled under reduced pressure
  5. customto remove solvent
  6. customgive a product which
  7. distillationdistilled at 187°C./0.2 mm
  8. customwas recrystallized from petroleum ether (b.p. 60° - 80°C.)

Sources & evidence

ORD record
ord-0606fed4107744fcaef2434f1f1ba163
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

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