Tetrahydrofuran → HCID 20354946, compound

HRID 1606056Notes

Reaction equation

HRID 1606056 reaction equation
[CH2:1]([S:6]([C:9]1[N:13]=[CH:12][NH:11][N:10]=1)(=[O:8])=[O:7])[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:14]([N:17]([CH2:21][CH:22]=[CH2:23])[C:18](Cl)=[O:19])[CH:15]=[CH2:16].O1CCCC1.C(N(CC)CC)C>CCOCC>[CH2:14]([N:17]([CH2:21][CH:22]=[CH2:23])[C:18]([N:11]1[CH:12]=[N:13][C:9]([S:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])(=[O:8])=[O:7])=[N:10]1)=[O:19])[CH:15]=[CH2:16]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 3449313Diallylcarbamyl chlorideHCID 178447784HCID 178447784, compound

Product 1

HCID 20354946HCID 20354946, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10.2 g. 3-pentylsulphonyl-1,2,4-triazole, 8.2 g. diallylcarbamoyl chloride, 75 ml. dry tetrahydrofuran and 7.5 ml. dry triethylamine was refluxed under anhydrous conditions for 1.5 hours. The reaction mixture was worked up as described in Example 1, using ether in place of methylene dichloride. An oily residue was obtained which was distilled under reduced pressure to give a product, b.p. 193° - 194°C./0.25 mm., which solidified on cooling. This product was recrystallized from petroleum ether (b.p. 60° - 80°C.) to give 1-diallylcarbamoyl-3-n-pentylsulphonyl-1,2,4-triazole, m.p. 28° - 30°C. Elemental analysis satisfactory.

Workup

  1. additionA mixture of 10.2 g
  2. customAn oily residue was obtained which
  3. distillationwas distilled under reduced pressure
  4. customto give a product, b.p. 193° - 194°C./0.25 mm
  5. temperatureon cooling
  6. customThis product was recrystallized from petroleum ether (b.p. 60° - 80°C.)

Sources & evidence

ORD record
ord-7ae9724ffc4c4510b1e1ef9c140ab6dd
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

Loading…