Propylamine → N-Butyl-N'-propylurea

HRID 466947Notes

Reaction equation

HRID 466947 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[CH2:5]([N:9]=[C:10]=[O:11])[CH2:6][CH2:7][CH3:8]>ClCCl>[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 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

205.8 Grams (3.48 moles) of n-propylamine and 250 ml of dichloromethane were charged to a round bottom flask equipped with stirrer, thermometer, reflux condenser and dropping funnel. 313.7 Grams (3.16 moles) of butyl isocyanate were added to the dropping funnel and then metered into the flask with stirring and strong external cooling (solid CO2 bath) at a rate slow enough to maintain the contents generally below 0° C. except for brief excursions to higher temperatures. The resulting mixture was left to stand overnight and then freed of solvent and lights under vacuum with a rotary evaporator leaving 462.3 g of crude product (92.6% crude yield). After further drying of a portion under vacuum a 97.6 area % purity was recorded by gas chromatography. The product contained substantially only one compound by gas chromatography. It melted at 70°-72° C.

Workup

  1. customequipped with stirrer
  2. temperaturethermometer, reflux condenser
  3. temperaturestrong external cooling (solid CO2 bath) at a rate slow enough
  4. temperatureto maintain the contents generally below 0° C. except for brief excursions to higher temperatures
  5. waitThe resulting mixture was left
  6. customfreed of solvent and lights under vacuum with a rotary evaporator

Sources & evidence

ORD record
ord-63ea547f32c14aacab029a3748b7bd11
Source dataset
uspto-grants-1992_10
Patent number
US05158808

Reaction notes

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