Diethylcarbamoyl chloride → HCID 20290130, compound

HRID 1606093Notes

Reaction equation

HRID 1606093 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][S:7][C:8]1[N:12]=[CH:11][NH:10][N:9]=1)[CH:2]=[CH2:3].C(N(CC)CC)C.[CH2:20]([N:22]([CH2:26][CH3:27])[C:23](Cl)=[O:24])[CH3:21]>O1CCCC1>[CH2:20]([N:22]([CH2:26][CH3:27])[C:23]([N:10]1[CH:11]=[N:12][C:8]([S:7][CH2:6][CH2:5][O:4][CH2:1][CH:2]=[CH2:3])=[N:9]1)=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 178459221HCID 178459221, compound

Product 1

HCID 20290130HCID 20290130, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.4 g. 3-(2-allyloxyethylthio)-1,2,4-triazole, 8ml. triethylamine 6.0 g. diethylcarbamoyl chloride in 40 ml. of tetrahydrofuran was heated under reflux for 15 hours. The cooled reaction mixture was filtered to remove triethylamine hydrochloride and the filtrate was evaporated under vacuum to remove the solvent. Further precipitation of amine hydrochloride was filtered off. The filtrate was dissolved in 50 ml. methylene chloride and washed with ice-cold N/10 sodium hydroxide, with N/10 hydrochloric acid and finally with ice-cold water. The solvent was removed by vacuum distillation to give a liquid product, 1-diethylcarbamoyl-3-(2-allyloxyethylthio)-1,2,4-triazole, b.p. 148° - 153°C./0.05 mm. GLC assay showed that the 1-isomer was present to the extent of 98.33%. Elemental analysis was 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 under vacuum
  6. customto remove the solvent
  7. customFurther precipitation of amine hydrochloride
  8. filtrationwas filtered off
  9. dissolutionThe filtrate was dissolved in 50 ml
  10. washmethylene chloride and washed with ice-cold N/10 sodium hydroxide
  11. customThe solvent was removed by vacuum distillation

Sources & evidence

ORD record
ord-74ac61885b394a608b4a3ab1456c939d
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

Loading…