Urea → HCID 19094847, compound

HRID 486333Notes

Reaction equation

HRID 486333 reaction equation
[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH2:19][C:20]([NH2:22])=[O:21].[OH-].[Na+]>CN1CCCC1=O.C1(OP(OC2C=CC=CC=2)OC2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:19][C:20]([NH2:22])=[O:21])=[O:16])=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 1176Urea2×HCID 14798Sodium HydroxideHCID 172314-(Octyloxy)benzoic acid

Product 1

HCID 19094847HCID 19094847, compound

Reagents, catalysts & solvents 2

HCID 7540Triphenyl phosphiteSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

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.

Workup

  1. additionA 500 ml 3-neck round bottom flask containing a magnetic stirrer
  2. temperatureThe mixture is heated to 120 deg C
  3. temperaturecooled
  4. customprecipitates the product
  5. customwhich is isolated by filtration
  6. additionrespectively) in addition to the conspicuous absence of any absorbance at 3490 cm-1 (acid O--H stretching)

Sources & evidence

ORD record
ord-ff9408c4f1f64d81bc2b440859e6597b
Source dataset
uspto-grants-1994_03
Patent number
US05292351

Reaction notes

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