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

HRID 2248415Notes

Reaction equation

HRID 2248415 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 isocyanate was 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-6cb89cf2679f47adbac7d1df95ee76a3
Source dataset
uspto-grants-1991_08
Patent number
US05039759

Reaction notes

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