Acetic Acid → N-(4-Hydroxyphenyl)urea

HRID 2094778Notes

Reaction equation

HRID 2094778 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(O)(=O)C.[O-:13][C:14]#[N:15].[Na+]>O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:14]([NH2:15])=[O:13])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4034-AminophenolHCID 517096Sodium Cyanate

Product 1

HCID 197742N-(4-Hydroxyphenyl)ureaYield 76.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-aminophenol (45 g, 0.4123 mol) was charged in water and acetic acid mixture (9:1) (450 vol) to obtain a clear solution. To this clear solution was added drop wise previously prepared solution of sodium cyanate (29.48 g, 0.45358 mol) in water over a period of 1 hour. The reaction mass obtained was stirred for 6 hours at ambient temperature and filtered to obtain solid. The solid was washed with water and vacuum dried to obtain the desired product, i.e., 1-(4-hydroxyphenyl)urea (48 g).

Workup

  1. customThe reaction mass obtained
  2. filtrationfiltered
  3. customto obtain solid
  4. washThe solid was washed with water and vacuum
  5. customdried

Sources & evidence

ORD record
ord-c803b88df38b4445867c03f6e664c632
Source dataset
uspto-grants-2013_05
Patent number
US08445687B2

Reaction notes

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