Tetrahydrofuran → HCID 20354997, compound

HRID 371585Notes

Reaction equation

HRID 371585 reaction equation
[CH:1]([S:5]([C:7]1[N:11]=[CH:10][NH:9][N:8]=1)=[O:6])([CH2:3][CH3:4])[CH3:2].[CH2:12]([N:15]([CH2:19][CH:20]=[CH2:21])[C:16](Cl)=[O:17])[CH:13]=[CH2:14].O1CCCC1.C(N(CC)CC)C>C(Cl)Cl>[CH2:12]([N:15]([CH2:19][CH:20]=[CH2:21])[C:16]([N:9]1[CH:10]=[N:11][C:7]([S:5]([CH:1]([CH2:3][CH3:4])[CH3:2])=[O:6])=[N:8]1)=[O:17])[CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 3449313Diallylcarbamyl chlorideHCID 178455553HCID 178455553, compound

Product 1

HCID 20354997HCID 20354997, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.76 g. 3-sec.butylsulphinyl-1,2,4-triazole, 5.31 g. diallylcarbamoyl chloride, 50 ml. dry tetrahydrofuran and 5 ml. dry triethylamine was kept under anhydrous conditions at room temperature for 72 hours. The reaction mixture was filtered and the filtrate evaporated under reduced pressure at room temperature to give a residual oil which was dissolved in methylene dichloride. The resulting solution was washed with water, dried over anhydrous sodium sulphate and distilled under reduced pressure at room temperature to give 1-diallylcarbamoyl-3-sec.butylsulphinyl-1,2,4-triazole as a residual oil, nD25 1.5268, for which a satisfactory elemental analysis was obtained.

Workup

  1. additionA mixture of 5.76 g
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate evaporated under reduced pressure at room temperature
  4. customto give a residual oil which
  5. washThe resulting solution was washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. distillationdistilled under reduced pressure at room temperature

Sources & evidence

ORD record
ord-7b499f774313477dac3fe81e8ed51225
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

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