4-Aminophenol → HCID 12238272, compound

HRID 2230251Notes

Reaction equation

HRID 2230251 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9]([N:11]=[C:12]=[O:13])[CH3:10].O>CN1CCCC1=O>[CH2:9]([NH:11][C:12]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 962WaterHCID 8022Ethyl isocyanate

Product 1

HCID 12238272HCID 12238272, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

10 g of 4-aminophenol (Mw=109.13; 0.0916 mol) are suspended in 100 cm3 of anhydrous N-methylpyrrolidone, under an inert atmosphere. 6.5 g of ethyl isocyanate (Mw=71.08; 0.0914 mol) are then added dropwise. The reaction mixture is brought to a temperature of 60° C. with stirring for two hours. The mixture is poured into one litre of water and the precipitate is then filtered off and dried. After recrystallization from ethanol, 9 g of a white powder are obtained, which corresponds to a yield of 55%. The melting point of the product obtained is 173.4° C. The 200 MHz 1H NMR spectrum and the elemental analysis are in accordance with the expected product.

Workup

  1. customis brought to a temperature of 60° C.
  2. filtrationthe precipitate is then filtered off
  3. customdried
  4. customAfter recrystallization from ethanol, 9 g of a white powder
  5. customare obtained
  6. customThe melting point of the product obtained
  7. customis 173.4° C

Sources & evidence

ORD record
ord-ef4f6d86b7f54727986a5f359a66d4fb
Source dataset
uspto-grants-2002_07
Patent number
US06423854B1

Reaction notes

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