Nitrogen → 3-(3-Bromo-5-chlorophenoxy)-4-chlorobenzene-1,2-diamine

HRID 505521노트

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HRID 505521 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:5][C:6]1[C:7]([N+:14]([O-])=O)=[C:8]([CH:10]=[CH:11][C:12]=1[Cl:13])[NH2:9].O.O.[Sn](Cl)Cl.N#N>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:5][C:6]1[C:12]([Cl:13])=[CH:11][CH:10]=[C:8]([NH2:9])[C:7]=1[NH2:14]

참가 물질

5

반응물 3

HCID 947NitrogenHCID 61436Stannous chloride dihydrateHCID 568336493-(3-Bromo-5-chlorophenoxy)-4-chloro-2-nitroaniline

생성물 1

HCID 568337453-(3-Bromo-5-chlorophenoxy)-4-chlorobenzene-1,2-diamine

시약·촉매·용매 1

HCID 887Methanol용매

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온도
75 °C

실험 절차

3-(3-bromo-5-chlorophenoxy)-4-chloro-2-nitroaniline (5.7 g, 15 mmol) and tin(II) chloride dihydrate (17 g, 75 mmol) were suspended in MeOH (100 mL) and heated to 75° C. under a reflux condenser and N2. After 10 hours, the reaction was allowed to cool to room temperature. The reaction was concentrated under reduced pressure, diluted with ethyl acetate (150 mL) and 10% aqueous sodium carbonate (250 mL) was added with vigorous stirring until the pH was 10. The mixture was filtered through celite. The resulting biphasic filtrate was separated and the aqueous extracted again with ethyl acetate (150 mL). The combined organic fractions were dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to yield the title product. LRMS (M+1)=348.7.

후처리

  1. temperatureto cool to room temperature
  2. concentrationThe reaction was concentrated under reduced pressure
  3. additiondiluted with ethyl acetate (150 mL) and 10% aqueous sodium carbonate (250 mL)
  4. additionwas added
  5. filtrationThe mixture was filtered through celite
  6. customThe resulting biphasic filtrate was separated
  7. extractionthe aqueous extracted again with ethyl acetate (150 mL)
  8. dry with materialThe combined organic fractions were dried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-4103d9c1fc284e76884f700574e170c9
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781454B2

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