Carbon Dioxide → 1-butyl-3-(2-hydroxyethyl)urea

HRID 466944Notes

Reaction equation

HRID 466944 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH2:5]([N:9]=[C:10]=[O:11])[CH2:6][CH2:7][CH3:8].C(=O)=O>ClCCl>[OH:2][CH2:1][CH2:3][NH:4][C:10]([NH:9][CH2:5][CH2:6][CH2:7][CH3:8])=[O:11]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 700EthanolamineHCID 8110Butyl isocyanate

Product 1

HCID 2519951-butyl-3-(2-hydroxyethyl)ureaYield 113%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

61.7 Grams (1 mole @ 99% purity) of ethanolamine and 170 grams of dichloromethane were charged to a flask equipped with stirrer, thermometer, feed tank, distillation head and condenser. 101 Grams (1 mole @ 98% purity) of butyl isocynate were fed dropwise with stirring and cooling (dry ice bath) during 1.5 hrs. such that the temperature of the reaction mixture was maintained at about 30° C. At this time some solid had been formed and it was redissolved by heating to 46° C. The mixture was stirred at 46° C. for an additional two hours and then freed of volatile materials by stripping at 90° C. and 2 mm Hg leaving 181 g of solid product. This material could be recrystallized from 2-butanone giving tiny white crystals melting at 67° C.

Workup

  1. customequipped with stirrer
  2. distillationthermometer, feed tank, distillation head and condenser
  3. customAt this time some solid had been formed
  4. dissolutionit was redissolved
  5. temperatureby heating to 46° C
  6. stirringThe mixture was stirred at 46° C. for an additional two hours
  7. customby stripping at 90° C.

Sources & evidence

ORD record
ord-e6adaa9225a7403292e04963affe31d5
Source dataset
uspto-grants-1992_10
Patent number
US05158808

Reaction notes

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