Toluene → HCID 533894, compound

HRID 973909Notes

Reaction equation

HRID 973909 reaction equation
[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][NH2:5])[CH3:2].[C:10](=O)([O:12]C)[NH2:11].C1(C)C=CC=CC=1>C([Sn](=O)CCCC)CCC.CO>[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][NH:5][C:10]([NH2:11])=[O:12])[CH3:2]

Participants

6

Reactant 3

HCID 1140TolueneHCID 77192-EthylhexylamineHCID 11722Methyl Carbamate

Product 1

HCID 533894HCID 533894, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 61221Dibutyltin oxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

Into a 300 ml reaction vessel equipped with a distillation apparatus were introduced 50 g of 2-ethylhexylamine, 29 g of methyl carbamate and 100 ml of toluene, and to the mixture was added 0.1 g of dibutyl tin oxide as a catalyst and heated with stirring. Methanol formed during the reaction was removed, when the reflux temperature was raised to 110° C., i.e., the boiling point of toluene, the distillation apparatus was taken off and instead a reflux condenser was attached and the mixture was refluxed by heating for 30 minutes with stirring, then allowed to cool. The toluene was distilled off under reduced pressure, and the residue was washed with n-hexane and collected by filtration to obtain 61 g of N-(2-ethylhexyl)urea.

Workup

  1. customInto a 300 ml reaction vessel
  2. customequipped with a distillation apparatus
  3. temperatureheated
  4. customwas removed
  5. temperaturethe mixture was refluxed
  6. temperatureby heating for 30 minutes
  7. stirringwith stirring
  8. temperatureto cool
  9. distillationThe toluene was distilled off under reduced pressure
  10. washthe residue was washed with n-hexane
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-8e461ebc2c304c5ab351036520c9b098
Source dataset
uspto-grants-1991_11
Patent number
US05066573

Reaction notes

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