Hydrochloric Acid → Urea, (2-hydroxy-4-methylphenyl)-

HRID 1741534Notes

Reaction equation

HRID 1741534 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].[NH2:10][C:11](N)=[O:12].Cl>O.C(O)(=O)C>[OH:8][C:7]1[CH:6]=[C:5]([CH3:9])[CH:4]=[CH:3][C:2]=1[NH:1][C:11]([NH2:10])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 1176UreaHCID 760822-Amino-5-methylphenol

Product 1

HCID 120120Urea, (2-hydroxy-4-methylphenyl)-Yield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To 13 ml of water, there were added 5.00 g (40.7 mmol) of 6-amino-m-cresol, 9.76 g of (162.6 mmol) of urea, 4 ml of conc. hydrochloric acid and 0.8 ml of a mixture (1:1 (v:v)) of conc. hydrochloric acid and glacial acetic acid, followed by heating under reflux for 1.5 hours. After cooling, 20 ml of water was added. The crystals thus precipitated were filtered and dried to thereby give 5.81 g (35.0 mmol) of N-(2-hydroxy-4-methylphenyl)urea as dark brown crystals. The yield was 86%. After recrystallizing from acetonitrile, 2.00 g of N-(2-hydroxy-4-methylphenyl)urea was obtained as pale purple crystals. The recovering yield was 34%.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. customThe crystals thus precipitated
  5. filtrationwere filtered
  6. customdried

Sources & evidence

ORD record
ord-bf95338779ae475fa9c9bc341d2d4a05
Source dataset
uspto-grants-1994_08
Patent number
US05334225

Reaction notes

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