Urea → N-(3-Hydroxy-2,6-dimethylphenyl)acetamide

HRID 1771634Notes

Reaction equation

HRID 1771634 reaction equation
N[C:2]1[C:3]([CH3:13])=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[C:5]([CH3:8])=[CH:6][CH:7]=1.N([O-])=[O:15].[Na+].NC(N)=O>OS(O)(=O)=O.O>[OH:15][C:2]1[C:3]([CH3:13])=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1176UreaHCID 847848N-(3-amino-2,6-dimethylphenyl)acetamideHCID 23668193Sodium Nitrite

Product 1

HCID 10419764N-(3-Hydroxy-2,6-dimethylphenyl)acetamideYield 40.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(3-amino-2,6-dimethyl-phenyl)acetamide (2 g, 11 mmol, 1.1 eq) in a mixture of H2SO4 (10 mL) and H2O (70 mL) at 0° C. was added a solution of NaNO2 (1 g, 14.6 mmol, 1.3 eq) in H2O (140 mL). The solution was stirred at 0° C. for 30 min then urea (425 mg, 7.1 mmol, 0.63 eq) was added. The reaction was poured into boiling water and the mixture stirred at 100° C. for 2 h. The aqueous phase was extracted with EtOAc, and the combined extracts were dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (MeOH:DCM, 0:1 to 1:20) to give the title compound as a white solid (800 mg, 40%).

Workup

  1. additionThe reaction was poured
  2. stirringthe mixture stirred at 100° C. for 2 h
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialthe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography (MeOH:DCM, 0:1 to 1:20)

Sources & evidence

ORD record
ord-c54590cb98004cc78ee649c48e695841
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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