Tetrahydrofuran → HCID 20354946, compound

HRID 371568Notes

Reaction equation

HRID 371568 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-bb6408893ba845a18e7ee2ad548b464c
Source dataset
uspto-grants-1978_05
Patent number
US04087269

Reaction notes

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