Propylamine → N-Butyl-N'-propylurea

HRID 466946Notes

Reaction equation

HRID 466946 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[CH2:5]([N:9]=[C:10]=[O:11])[CH2:6][CH2:7][CH3:8]>C1(C)C=CC=CC=1>[CH2:1]([NH:4][C:10]([NH:9][CH2:5][CH2:6][CH2:7][CH3:8])=[O:11])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 8110Butyl isocyanate

Product 1

HCID 14836212N-Butyl-N'-propylureaYield 96.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

205.76 Grams (3.48 moles) of n-propylamine were charged to a 1-1., round bottom flask equipped with stirrer, thermometer, reflux condenser and addition funnel. 313.7 Grams (3.16 moles) of butyl isocyanate were charged to the addition funnel and added to the flask with stirring at a rate which maintained the contents at about 60°-65° C. Toluene was added to dissolve the solid product for transfer to a stripping vessel. The crude product solution was about 92 area % ureas on a solvent-free basis by gas chromatography. The crude product solution was freed of most of the solvent and lights under vacuum with a rotary evaporator leaving 480.6 g of pale yellow solid melting from 68°-70° C. Infrared analysis showed a clean spectrum in agreement with the proposed structure's functionality. The gas chromatograph showed three, major peaks in a 1:2:1 ratio indicating possible `scrambling` of alkyl groups and a statistically determined ratio of products.

Workup

  1. custom, round bottom flask equipped with stirrer
  2. temperaturethermometer, reflux
  3. additioncondenser and addition funnel
  4. additionadded to the flask
  5. temperaturemaintained the contents at about 60°-65° C
  6. dissolutionto dissolve the solid product for transfer to a stripping vessel
  7. customwith a rotary evaporator

Sources & evidence

ORD record
ord-d321800ca17443728eb2ff137bacbafd
Source dataset
uspto-grants-1992_10
Patent number
US05158808

Reaction notes

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