4-Aminophenol → 1-(4-hydroxyphenyl)-3-methylurea

HRID 64950Notes

Reaction equation

HRID 64950 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1>C(#N)C.CN(C)C=O>[OH:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3]([NH:2][CH3:1])=[O:4])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 4034-AminophenolHCID 12228Methyl Isocyanate

Product 1

HCID 3496051-(4-hydroxyphenyl)-3-methylureaYield 51.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of methyl isocyanate (6 g) in acetonitrile (10 ml) was added dropwise to a solution of 4-aminophenol (10.9 g) in N,N-dimethylformamide (50 ml) at 10° C. to 20° C. The mixture was stirred at 25° C. to 35° C. for 12 hours and evaporated under reduced pressure. Water (100 ml) was added to the resulting syrup and the mixture was stirred for 30 minutes. The mixture became thick in the course of stirring. The solid substance was collected by filtration, washed with cold water and recrystallized from aqueous alcohol to give 8.6 g of N-(4-hydroxyphenyl)-N'-methylurea of melting point 169°-171° C.

Workup

  1. customevaporated under reduced pressure
  2. additionWater (100 ml) was added to the resulting syrup
  3. stirringthe mixture was stirred for 30 minutes
  4. stirringof stirring
  5. filtrationThe solid substance was collected by filtration
  6. washwashed with cold water
  7. customrecrystallized from aqueous alcohol

Sources & evidence

ORD record
ord-7d617a9fe6534107b35252a25a55135b
Source dataset
uspto-grants-1986_09
Patent number
US04611060

Reaction notes

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