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

HRID 51859

반응식

HRID 51859 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1118Sulfuric Acid용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
7.5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c3efeb78626247de87e868c249c3882b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713499B2

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