Triethylamine → HCID 20290106, compound

HRID 1606091Notes

Reaction equation

HRID 1606091 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). This 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. customThis solid was collected
  10. customrecrystallized from 100 ml

Sources & evidence

ORD record
ord-c87d7e10935e439b93f3c03fb5964875
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

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