Reaction #573515

Reaction equation

urea

p-(n-octyloxy)benzoic acid

urea

sodium hydroxide

→

p-(n-octyloxy)benzoylurea

Solvents

N-methylpyrrolidone

triphenylphosphite

Conditions

Workup

1. 1
   workup.ADDITIONA 500 ml 3-neck round bottom flask containing a magnetic stirrer
2. 2
   TemperatureThe mixture is heated to 120 deg C
3. 3
   Temperaturecooled
4. 4
   Otherprecipitates the product
5. 5
   Otherwhich is isolated by filtration
6. 6
   workup.ADDITIONrespectively) in addition to the conspicuous absence of any absorbance at 3490 cm-1 (acid O--H stretching)

Procedure

A 500 ml 3-neck round bottom flask containing a magnetic stirrer, thermometer, and a reflux condensor with a gas egress tube for a nitrogen blanket is charged with a one part apiece of p-(n-octyloxy)benzoic acid and urea dissolved in 15 parts N-methylpyrrolidone containing 0.01wt percent triphenylphosphite. The mixture is heated to 120 deg C. for approximately 2-5 hours and then cooled. The addition of a copious amount of 3M aqueous sodium hydroxide to a cooled solution precipitates the product, which is isolated by filtration. Infrared absorbance at 3250 cm-1 (urea N--H stretching) and at 1705 cm-1 and 1640 cm-1 (amide and urea C=O stretching, respectively) in addition to the conspicuous absence of any absorbance at 3490 cm-1 (acid O--H stretching) confirm the chemical transformation.

Source