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

HRID 1771634

Reaktionsgleichung

Reaktionsgleichung von HRID 1771634
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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 10419764N-(3-Hydroxy-2,6-dimethylphenyl)acetamideAusbeute 40,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c54590cb98004cc78ee649c48e695841
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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