Tetrahydrofuran → 1-(N-n-pentyl-N-propylcarbamoyl)-3-ethylsulphonyl-1,2,4-triazole

HRID 371592Notes

Reaction equation

HRID 371592 reaction equation
[CH2:1]([S:3]([C:6]1[N:10]=[CH:9][NH:8][N:7]=1)(=[O:5])=[O:4])[CH3:2].[CH2:11]([N:16]([CH2:20][CH2:21][CH3:22])[C:17](Cl)=[O:18])[CH2:12][CH2:13][CH2:14][CH3:15].O1CCCC1>C(N(CC)CC)C>[CH2:11]([N:16]([CH2:20][CH2:21][CH3:22])[C:17]([N:8]1[CH:9]=[N:10][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[N:7]1)=[O:18])[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 54493124N-n-pentyl-N-propylcarbamoyl chlorideHCID 178477666HCID 178477666, compound

Product 1

HCID 203549391-(N-n-pentyl-N-propylcarbamoyl)-3-ethylsulphonyl-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 4.83 g. 3-ethylsulphonyl-1,2,4-triazole, 6.0 g. N-n-pentyl-N-propylcarbamoyl chloride, 40 ml. dry tetrahydrofuran and 6 ml. dry triethylamine was refluxed under anhydrous conditions for 24 hours. The cooled reaction mixture was filtered. The filtrate was distilled under reduced pressure to give 1-(N-n-pentyl-N-propylcarbamoyl)-3-ethylsulphonyl-1,2,4-triazole as a residual oil, nD25 1.4967. (96.5% 1-isomer by GLC assay). Elemental analysis satisfactory.

Workup

  1. additionA mixture of 4.83 g
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. distillationThe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-341c57c70cc340269d9ea1965ea1e52b
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

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