Urea → Benzenamine, 4-methoxy-3-nitro-

HRID 51859

反応式

HRID 51859 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.NC(N)=O.[N+:14]([O-])([O-:16])=[O:15].[K+].[OH-].[Na+]>S(=O)(=O)(O)O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15]

参加物

7

反応物 4

HCID 1176UreaHCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 24434Potassium Nitrate

生成物 1

HCID 123071Benzenamine, 4-methoxy-3-nitro-収率 77%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
7.5 °C

実験手順

To a stirred solution of 30.0 g (244 mmol) p-anisidine in 105 ml concentrated sulfuric acid at 0° C. was added 17.6 g (292 mmol) urea. After stirring for 1 h, a solution of 27.1 g (268 mmol) potassium nitrate in 47 ml concentrated sulfuric acid was then added dropwise over 1 h while the reaction mixture was maintained at 5-10° C. The mixture was then poured onto ice, and sodium hydroxide pellets added portionwise with stirring until the pH was 14. Ethyl acetate was then added and the phases were separated. The organic phase was washed with water and then with brine, dried over sodium sulfate, and concentrated in vacuo to afford 31.4 g (77%) 4-methoxy-3-nitro-phenylamine as an orange solid. EI-MS m/e (%): 169 (M+, 100), 153 ([M-CH3]+, 10), 92 (21).

後処理

  1. additionadded portionwise
  2. stirringwith stirring until the pH was 14
  3. customthe phases were separated
  4. washThe organic phase was washed with water
  5. dry with materialwith brine, dried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c3efeb78626247de87e868c249c3882b
出典データセット
uspto-grants-2004_03
特許番号
US06713499B2

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