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

HRID 1771634

反応式

HRID 1771634 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c54590cb98004cc78ee649c48e695841
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

関連ノート

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