Toluene → HCID 533894, compound

HRID 1089409Notes

Reaction equation

HRID 1089409 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, 50 g of 2-ethylhexylamine, 29 g of methyl carbamate and 100 ml of toluene were placed, 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. temperatureheated
  3. customwas removed
  4. temperaturethe mixture was refluxed
  5. temperatureby heating for 30 minutes
  6. stirringwith stirring
  7. temperatureto cool
  8. distillationThe toluene was distilled off under reduced pressure
  9. washthe residue was washed with n-hexane
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1858b73381794dca9195d2912187317d
Source dataset
uspto-grants-1990_10
Patent number
US04966835

Reaction notes

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