Tetrahydrofuran → 1-Dipropylcarbamoyl-3-propylsulphinyl-1,2,4-triazole

HRID 1606066Notes

Reaction equation

HRID 1606066 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:14]([CH2:18][CH2:19][CH3:20])[C:15](Cl)=[O:16])[CH2:12][CH3:13].O1CCCC1>C(N(CC)CC)C>[CH2:11]([N:14]([CH2:18][CH2:19][CH3:20])[C:15]([N:8]1[CH:9]=[N:10][C:6]([S:4]([CH2:1][CH2:2][CH3:3])=[O:5])=[N:7]1)=[O:16])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 3015348Dipropylcarbamoyl chlorideHCID 1784610023-Propylsulphinyl-1,2,4-triazole

Product 1

HCID 203551191-Dipropylcarbamoyl-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, 6.0 ml. dipropylcarbamoyl chloride, 25 ml. dry tetrahydrofuran and 7.5 ml. dry triethylamine was refluxed under anhydrous conditions for 2 hours. The cooled reaction mixture was filtered and the filtrate distilled under reduced pressure to give an oily residue which crystallized on trituration with petroleum ether (b.p. 60° - 80°C.). The resulting solid product was recrystallized from petroleum ether (b.p. 60° - 80°C.) to give 1-dipropylcarbamoyl-3-propylsulphinyl-1,2,4-triazole, m.p. 50° - 52°C. Elemental analysis satisfactory.

Workup

  1. additionA mixture of 4.8 g
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. distillationthe filtrate distilled under reduced pressure
  5. customto give an oily residue which
  6. customcrystallized on trituration with petroleum ether (b.p. 60° - 80°C.)
  7. customThe resulting solid product was recrystallized from petroleum ether (b.p. 60° - 80°C.)

Sources & evidence

ORD record
ord-34b1b1af4b86493b80c98c13733f3c02
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

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