Diethylcarbamoyl chloride → 1-Diethylcarbamoyl-3-propylthio-1,2,4-triazole

HRID 371589Notes

Reaction equation

HRID 371589 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:12]([CH2:16][CH3:17])[C:13](Cl)=[O:14])[CH3:11].O1CCCC1>C(N(CC)CC)C>[CH2:10]([N:12]([CH2:16][CH3:17])[C:13]([N:7]1[CH:8]=[N:9][C:5]([S:4][CH2:1][CH2:2][CH3:3])=[N:6]1)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 8028TetrahydrofuranHCID 178460806HCID 178460806, compound

Product 1

HCID 201633721-Diethylcarbamoyl-3-propylthio-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 7.2 g. 3-propylthio-1,2,4-triazole, 6.8 g. diethylcarbamoyl chloride, 35 ml. dry tetrahydrofuran and 9 ml. dry triethylamine was refluxed under anhydrous conditions for 72 hours. The reaction mixture was worked up as described in Example 1 to produce a residual oil. This oil was distilled under reduced pressure to give 1-diethylcarbamoyl-3-propylthio-1,2,4-triazole, b.p. 118° - 121° C./0.2 mm. (89.9% 1-isomer by GLC assay). Elemental analysis satisfactory.

Workup

  1. additionA mixture of 7.2 g
  2. customto produce a residual oil
  3. distillationThis oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-c6486284eb4c417e8f2685079eeeed0f
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

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