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

HRID 371560Notes

Reaction equation

HRID 371560 reaction equation
[CH2:1]([S:4][C:5]1[N:9]=[CH:8][NH:7][N:6]=1)[CH2:2][CH3:3].[CH2:10]([N:13]([CH2:17][CH:18]=[CH2:19])[C:14](Cl)=[O:15])[CH:11]=[CH2:12].O1CCCC1>C(N(CC)CC)C>[CH2:10]([N:13]([CH2:17][CH:18]=[CH2:19])[C:14]([N:7]1[CH:8]=[N:9][C:5]([S:4][CH2:1][CH2:2][CH3:3])=[N:6]1)=[O:15])[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 3449313Diallylcarbamyl chlorideHCID 178460806HCID 178460806, compound

Product 1

HCID 203550941-Diallylcarbamoyl-3-propylthio-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 5.75 g. 3-propylthio-1,2,4-triazole, 6.8 g. diallylcarbamoyl chloride, 25 ml. dry tetrahydrofuran and 8 ml. dry triethylamine was refluxed under anhydrous conditions for 3 hours. The reaction mixture was worked up as described in Example 1 to produce an oil which was distilled under reduced pressure to give 1-diallylcarbamoyl-3-propylthio-1,2,4-triazole, b.p. 134° - 135° C./0.1 mm. Gas-liquid chromatographic (GLC) assay indicated a content of 1-isomer of 94.2%. Elemental analysis satisfactory.

Workup

  1. additionA mixture of 5.75 g
  2. customto produce an oil which
  3. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-75c2f898eb4e42d580103087a09f1e8d
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

Loading…