Tetrahydrofuran → HCID 20354921, compound

HRID 1606072Notes

Reaction equation

HRID 1606072 reaction equation
[CH:1]([S:5]([C:8]1[N:12]=[CH:11][NH:10][N:9]=1)(=[O:7])=[O:6])([CH2:3][CH3:4])[CH3:2].[CH2:13]([N:16]([CH2:20][CH:21]=[CH2:22])[C:17](Cl)=[O:18])[CH:14]=[CH2:15].O1CCCC1>C(N(CC)CC)C>[CH2:13]([N:16]([CH2:20][CH:21]=[CH2:22])[C:17]([N:10]1[CH:11]=[N:12][C:8]([S:5]([CH:1]([CH2:3][CH3:4])[CH3:2])(=[O:6])=[O:7])=[N:9]1)=[O:18])[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 3449313Diallylcarbamyl chlorideHCID 178455594HCID 178455594, compound

Product 1

HCID 20354921HCID 20354921, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 9.5 g. 3-sec.butylsulphonyl-1,2,4-triazole, 7.97 g. diallylcarbamoyl chloride, 50 ml. dry tetrahydrofuran and 7.5 ml. dry triethylamine was refluxed under anhydrous conditions for 5 hours. The reaction mixture was worked up by a method analogous to that described in Example 1 to give an oil which was not distilled but was heated under reduced pressure. (95°C/0.1 mm.) for 4 hours to remove traces of volatile material. The resulting product, 1-diallylcarbamoyl-3-sec.butylsulphonyl-1,2,4-triazole, was obtained as an oil, nD26 1.5174. (98.9% 1-isomer by GLC assay). Elemental analysis satisfactory.

Workup

  1. additionA mixture of 9.5 g
  2. customto give an oil which
  3. distillationwas not distilled
  4. temperaturewas heated under reduced pressure
  5. custom(95°C/0.1 mm.) for 4 hours to remove traces of volatile material

Sources & evidence

ORD record
ord-926e64caf9134cd7abd9e201cc02a51e
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

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