Sodium Sulfite → 4-(4-Nitrophenyl)-morpholin-3-ON

HRID 33253

반응식

HRID 33253 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Mn]([O-])(=O)(=O)=[O:17].[K+].[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][C:11]2=[O:17])=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

7

반응물 3

HCID 24437Sodium SulfiteHCID 252224-(4-Nitrophenyl)morpholineHCID 516875Potassium Permanganate

생성물 1

HCID 114473754-(4-Nitrophenyl)-morpholin-3-ON

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 10 g 4-(4-Nitro-phenyl)-morpholine in 200 ml DCM, 32 g Benzyl-triethyl-ammonium chloride and 22.7 g potassium permanganate (325 mesh) were cautiously added at RT. After stirring for 1 h at RT the reaction mixture was heated to reflux for 10 h. Then a solution of 95 g Na2SO3 in 450 ml water were added under ice cooling and vigourous stirring. The mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure. The yellow solid was stirred with 250 ml water and the precipitated product was collected by filtration. This crude product was purified by chromatography on silica gel eluting with a gradient of DCM/MeOH 100%->50%. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 2.6 g.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 10 h
  3. filtrationThe mixture was filtered through a pad of celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. stirringThe yellow solid was stirred with 250 ml water
  6. filtrationthe precipitated product was collected by filtration
  7. customThis crude product was purified by chromatography on silica gel eluting with a gradient of DCM/MeOH 100%->50%
  8. additionThe fractions containing the product
  9. customthe solvent evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-18b6c2a7837f455a90993e970e942924
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429581B2

연결된 노트

불러오는 중…