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

HRID 371583Notes

Reaction equation

HRID 371583 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. (96.0% 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-9aaf71249615418a8905e223ed9460c5
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

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