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

HRID 1771634

반응식

HRID 1771634 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매3회HCID 1118Sulfuric Acid용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c54590cb98004cc78ee649c48e695841
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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