Ammonia → HCID 18954420, compound

HRID 1492067Notes

Reaction equation

HRID 1492067 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].N[C:7](N)=[O:8].[CH2:10]([CH:12]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:13][OH:14])[CH3:11].C([Sn](=O)CCCC)CCC.N>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:7](=[O:8])[O:14][CH2:13][CH:12]([CH2:10][CH3:11])[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 1176UreaHCID 77202-EthylhexanolHCID 80182-MethoxyethylamineHCID 61221Dibutyltin oxide

Product 1

HCID 18954420HCID 18954420, compound

Conditions

Temperature
180 °C

Procedure

225 g (3.0 mols) of 2-methoxyethylamine, 180 g (3.0 mols) of urea, 1,950 g (15 mols) of 2-ethylhexanol and 3 g of dibutyltin oxide are introduced into a 4 liter round-bottom flask equipped with reflux condenser, and the mixture is heated while stirring. A vigorous evolution of ammonia sets in at temperatures above 110° C. Ammonia gas is removed through the reflux condenser and absorbed in water. Over the course of 3 hours, the temperature is increased to 180° C. (reflux), the elimination of ammonia virtually ceasing. After a further 2 hours under reflux, the mixture is freed of remaining ammonia by flushing with nitrogen and subsequently subjected to fractional distillation. After a first cut comprising mainly ethylhexanol, the desired urethane distills over at 98°-100° C./0.1 mbar as a colorless liquid (yield: 617 g=89% of theory). 27 g of a brown liquid remain as the distillation residue and solidify to give a pasty product on cooling.

Workup

  1. customequipped
  2. temperaturewith reflux condenser
  3. temperaturethe mixture is heated
  4. customin at temperatures above 110° C
  5. customAmmonia gas is removed through the reflux condenser
  6. customabsorbed in water
  7. temperature(reflux)
  8. temperatureAfter a further 2 hours under reflux
  9. customby flushing with nitrogen
  10. distillationsubsequently subjected to fractional distillation
  11. distillationAfter a first cut comprising mainly ethylhexanol, the desired urethane distills over at 98°-100° C./0.1 mbar as a colorless liquid (yield: 617 g=89% of theory)
  12. customto give a pasty product
  13. temperatureon cooling

Sources & evidence

ORD record
ord-159029874f4547bdab799f0af2fe3275
Source dataset
uspto-grants-1994_12
Patent number
US05371271

Reaction notes

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