Tetrahydrofuran → 1-Diallylcarbamoyl-3-sec.butylthio-1,2,4-triazole

HRID 1606071Notes

Reaction equation

HRID 1606071 reaction equation
[CH:1]([S:5][C:6]1[N:10]=[CH:9][NH:8][N:7]=1)([CH2:3][CH3:4])[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>CCOCC>[CH2:11]([N:14]([CH2:18][CH:19]=[CH2:20])[C:15]([N:8]1[CH:9]=[N:10][C:6]([S:5][CH:1]([CH2:3][CH3:4])[CH3:2])=[N:7]1)=[O:16])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 3449313Diallylcarbamyl chlorideHCID 178454954HCID 178454954, compound

Product 1

HCID 203550531-Diallylcarbamoyl-3-sec.butylthio-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.9 g. 3-sec.butylthio-1,2,4-triazole, 8.0 g. diallylcarbamoyl chloride, 100 ml. dry tetrahydrofuran and 8 ml. dry triethylamine was refluxed under anhydrous conditions for 24 hours. The reaction mixture was worked up as described in Example 1, using ether in place of methylene dichloride, to produce an oil which was distilled under reduced pressure to give 1-diallylcarbamoyl-3-sec.butylthio-1,2,4-triazole, b.p. 121° - 123°C./0.1 mm. (96% 1-isomer by GLC assay). Elemental analysis satisfactory.

Workup

  1. additionA mixture of 7.9 g
  2. customto produce an oil which
  3. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-6d3962cc1af6424dbef9894410f05440
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

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