Hydrochloric Acid → N-(3-tert-Butyl-2-hydroxy-5-methoxyphenyl)-N'-phenylurea

HRID 1457570Notes

Reaction equation

HRID 1457570 reaction equation
Cl.[C:2]1([NH:8][C:9](=[O:27])[NH:10][C:11]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:12]=2[O:13]COC)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[C:2]1([NH:8][C:9](=[O:27])[NH:10][C:11]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([C:23]([CH3:24])([CH3:26])[CH3:25])[C:12]=2[OH:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22099424[2-(3-Phenylureido)-4-methoxy-6-tert-butylphenoxy]methoxymethane

Product 1

HCID 22099432N-(3-tert-Butyl-2-hydroxy-5-methoxyphenyl)-N'-phenylureaYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. hydrochloric acid (1.5 ml) was added to 30 ml of a methanol solution containing 2.2 g of [2-(3-phenyl-ureido)-4-methoxy-6-tert-butylphenoxy]methoxymethane and the mixture was stirred at room temperature for 1.5 hours. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. Hexane was added to the residue and the resulting crystals were collected by filtration and recrystallized from a mixed solution of ethyl acetate and hexane to give 1.6 g of 2-(3-phenylureido)-4-methoxy-6-tert-butylphenol (yield: 83%, melting point: 147°-149° C., IR: 3400, 3350, 1670 cm-1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. additionHexane was added to the residue
  7. filtrationthe resulting crystals were collected by filtration
  8. customrecrystallized from a mixed solution of ethyl acetate and hexane

Sources & evidence

ORD record
ord-61103e6bc4f34402a8feff31b23650e2
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

Loading…