Triethylamine → HCID 20290106, compound

HRID 1413657Notes

Reaction equation

HRID 1413657 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][S:5]([C:8]1[N:12]=[CH:11][NH:10][N:9]=1)(=[O:7])=[O:6].C(N(CC)CC)C.[CH2:20]([N:22]([CH:26]([CH3:28])[CH3:27])[C:23](Cl)=[O:24])[CH3:21]>O1CCCC1>[CH2:20]([N:22]([CH:26]([CH3:28])[CH3:27])[C:23]([N:10]1[CH:11]=[N:12][C:8]([S:5]([CH2:4][CH2:3][O:2][CH3:1])(=[O:6])=[O:7])=[N:9]1)=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21185221ethyl(isopropyl)carbaMic chlorideHCID 178496539HCID 178496539, compound

Product 1

HCID 20290106HCID 20290106, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.03 mole of 3-(2-methoxyethylsulphonyl)-1,2,4-triazole, 6 ml. of triethylamine and 0.033 mole of N-ethyl-N-isopropylcarbamoyl chloride in 40 ml. of dry tetrahydrofuran was heated under reflux for 15 hours. The cooled reaction mixture was filtered to remove triethylamine hydrochloride and the filtrate was evaporated to remove solvent. The product crystallized on cooling and treatment with 100 ml. of petroleum ether (b.p. 62°-68° C.). Thin solid was collected and recrystallized from 100 ml. benzene petroleum ether (b.p. 40°-60° C.) to give 1-(N-ethyl-N-isopropylcarbamoyl)-3-(2-methoxyethylsulphonyl)-1,2,4-triazole, m.p. 64°-65° C. Elemental analysis satisfactory.

Workup

  1. temperatureunder reflux for 15 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customto remove triethylamine hydrochloride
  5. customthe filtrate was evaporated
  6. customto remove solvent
  7. customThe product crystallized
  8. temperatureon cooling
  9. customThin solid was collected
  10. customrecrystallized from 100 ml

Sources & evidence

ORD record
ord-3f0d847ccff34815807183b4c75ff231
Source dataset
uspto-grants-1981_02
Patent number
US04251262

Reaction notes

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