4-Aminophenol → N-(4-Hydroxyphenyl)-N'-octadecylurea

HRID 1608547Notes

Reaction equation

HRID 1608547 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[CH2:9]([N:27]=[C:28]=[O:29])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C(C(C)=O)C>[OH:8][C:3]1[CH:4]=[CH:5][C:6]([NH:7][C:28]([NH:27][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:29])=[CH:1][CH:2]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 66988Octadecyl isocyanate2×

Product 1

HCID 21226366N-(4-Hydroxyphenyl)-N'-octadecylureaYield 95.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Under a nitrogen atmosphere, p-aminophenol (109 g) was suspended in methyl ethyl ketone (2000 ml) and the suspension was heated to 70° C. n-Octadecyl isocyanate (296 g) was added dropwise to the suspension with vigorous stirring over a period of about 30 minutes. In this case, since heat of reaction was generated, n-octadecyl isocyanate was added dropwise at a rate at which the temperature of the reaction mixture was kept at 70°-75° C. After completion of the addition, the temperature of the reaction mixture was raised to 75°-80° C. and the reaction was allowed to proceed for further 30 minutes. After completion of the reaction, the reaction mixture was tooled to room temperature to precipitate a white solid. The solvent was removed by filtration and the residue was dried under reduced pressure to obtain a nearly pure desired product (385 g). Yield 95%; m.p. 144° C.

Workup

  1. additionwas added dropwise to the suspension
  2. temperatureIn this case, since heat of reaction
  3. customwas kept at 70°-75° C
  4. additionAfter completion of the addition
  5. temperaturethe temperature of the reaction mixture was raised to 75°-80° C.
  6. waitto proceed for further 30 minutes
  7. customAfter completion of the reaction
  8. customwas tooled to room temperature
  9. customto precipitate a white solid
  10. customThe solvent was removed by filtration
  11. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-5902578f0bfd49c6b209272135ce28a5
Source dataset
uspto-grants-1995_03
Patent number
US05395815

Reaction notes

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