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

HRID 505548

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HRID 505548 반응식
[Br:1][C:2]1[C:3]([Cl:21])=[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[C:3]([Cl:21])=[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 684277843-(3-Bromo-2,5-dichlorophenoxy)-4-chloro-2-nitroaniline

생성물 1

HCID 684264093-(3-Bromo-2,5-dichlorophenoxy)-4-chlorobenzene-1,2-diamine

시약·촉매·용매 1

HCID 887Methanol용매

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온도
75 °C

실험 절차

3-(3-bromo-2,5-dichlorophenoxy)-4-chloro-2-nitroaniline (2.68 g, 6.50 mmol) and tin(II) chloride dihydrate (7.33 g, 32.5 mmol) were suspended in MeOH (50 mL) and heated to 75° C. under a reflux condenser and N2. After 11 hours, the reaction mixture was allowed to cool to room temperature, and concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate (150 mL), after which 10% aqueous sodium carbonate (250 mL) was added with vigorous stirring until the pH was 10. The resulting suspension was filtered through celite, the filtrate was extracted with ethyl acetate. The combined organic fractions were dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to yield the title compound. LRMS (M+1)=382.5.

후처리

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe resulting residue was diluted with ethyl acetate (150 mL)
  4. additionafter which 10% aqueous sodium carbonate (250 mL) was added
  5. filtrationThe resulting suspension was filtered through celite
  6. extractionthe filtrate was extracted with ethyl acetate
  7. dry with materialThe combined organic fractions were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-289fa66c32454393bc1518d1456b2362
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781454B2

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