Triethylamine → HCID 20290177, compound

HRID 1606088Notes

Reaction equation

HRID 1606088 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][S:6]([C:9]1[N:13]=[CH:12][NH:11][N:10]=1)(=[O:8])=[O:7])[CH3:2].[CH2:14]([N:17]([CH2:21][CH:22]=[CH2:23])[C:18](Cl)=[O:19])[CH:15]=[CH2:16].C(N(CC)CC)C>O1CCCC1>[CH2:14]([N:17]([CH2:21][CH:22]=[CH2:23])[C:18]([N:11]1[CH:12]=[N:13][C:9]([S:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])(=[O:8])=[O:7])=[N:10]1)=[O:19])[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3449313Diallylcarbamyl chlorideHCID 178468149HCID 178468149, compound

Product 1

HCID 20290177HCID 20290177, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.1 g. 3-(2-ethoxyethylsulphonyl)-1,2,4-triazole, 3.5 g. diallylcarbamoyl chloride and 4 ml. triethylamine in 40 ml. dry tetrahydrofuran was refluxed under anhydrous conditions for 15 hours. The cooled reaction mixture was filtered to remove triethylamine hydrochloride and the filtrate was evaporated to remove solvent. The residue was triturated with petroleum ether (b.p. 40° - 60°C.) to give a solid product. This product was collected and recrystallised from ether/petroleum ether b.p. 40° - 60°C. to give 1-diallylcarbamoyl-3-(2-ethoxyethylsulphonyl)-1,2,4-triazole, m.p. 62° - 63°C. Elemental analysis satisfactory.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. customto remove triethylamine hydrochloride
  4. customthe filtrate was evaporated
  5. customto remove solvent
  6. customThe residue was triturated with petroleum ether (b.p. 40° - 60°C.)
  7. customto give a solid product
  8. customThis product was collected
  9. customrecrystallised from ether/petroleum ether b.p. 40° - 60°C.

Sources & evidence

ORD record
ord-c3bd3d20cb2041c2ab4788f4683753b0
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

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