Urea → 2-Ethyl-5-nitrophenol

HRID 2392647노트

반응식

HRID 2392647 반응식
[CH2:1]([C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1N)[CH3:2].N([O-])=[O:14].[Na+].NC(N)=O.[OH-].[Na+]>S(=O)(=O)(O)O.O>[CH2:1]([C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[OH:14])[CH3:2]

참가 물질

7

반응물 4

HCID 1176UreaHCID 14798Sodium HydroxideHCID 41554782-Ethyl-5-nitroanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 189800772-Ethyl-5-nitrophenol수율 58%

시약·촉매·용매 2

HCID 962Water용매2회HCID 1118Sulfuric Acid용매

반응 조건

온도
80 °C

실험 절차

A solution of 2-ethyl-5-nitroaniline (prepared as described by E. Dyszer et al, Przemysl. Chem 42 (8) 433-5 (1963)) (5 g) in concentrated sulphuric acid (27 ml) and water (160 ml) at 0° C., was treated with sodium nitrite (2.3 g) in water (5 ml) over 5 minutes with stirring. After 1/4 h at 0° C., urea (2 g) was added and the mixture heated to 80° C. for 2 h. After stirring overnight at room temperature, the pH was adjusted to pH 10-12 with 10% sodium hydroxide, and the mixture extracted into ethyl acetate. The organic phase was dried (Na2SO4) and the solvent evaporated under reduced pressure. Flash column chromatography on silica gel, eluting with ethyl acetate and 60°-80° C. petroleum-ether gave the title compound (2.91 g, 58%).

후처리

  1. waitAfter 1/4 h at 0° C.
  2. stirringAfter stirring overnight at room temperature
  3. extractionthe mixture extracted into ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customthe solvent evaporated under reduced pressure
  6. washFlash column chromatography on silica gel, eluting with ethyl acetate and 60°-80° C. petroleum-ether

출처 및 근거

ORD 기록
ord-e421eaf942354ad2ae96d9137f0d0465
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05801170

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