Hydrochloric Acid → (3E,5E)-1-methyl-3,5-bis((4-nitrophenyl)methylidene]azepan-4-one

HRID 1508265

반응식

HRID 1508265 반응식
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH2:4][CH2:3]1.Cl.[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([O-:13])=[O:12].OS(O)(=O)=O>C(O)(=O)C.O>[CH3:1][N:2]1[CH2:8][CH2:7]/[C:6](=[CH:18]\[C:17]2[CH:20]=[CH:21][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)/[C:5](=[O:9])/[C:4](=[CH:18]/[C:17]2[CH:20]=[CH:21][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)/[CH2:3]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 1118Sulfuric Acid5회HCID 2625861-Methylazepan-4-one

생성물 1

HCID 71523484(3E,5E)-1-methyl-3,5-bis((4-nitrophenyl)methylidene]azepan-4-one

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

N-methylazepan-4-one.HCl (50 mg, 0.30 mmol) and 4-nitrobenzaldehyde were dissolved in acetic acid (5 mL) and stirred for 10 min, then conc. H2SO4 (50 μL) was added slowly and the mixture was stirred at rt overnight. More concentrated H2SO4 (100 μL) was added and stirring was continued at rt for 6 h. Additional 500 μL of concentrated H2SO4 was added and the reaction stirred overnight. A further 350 μL of conc. H2SO4 was added and stirring continued for additional 5 h, during which period further H2SO4 was added in two portions (500 μL and 250 μL). Then water (3× reaction volume) was added and the mixture was stirred until rt was reached. The reaction mixture was extracted with ethyl acetate (3× reaction volume). The phases were separated and the organic phase concentrated to yield a dark yellow viscous oil. The crude product was purified by preparative HPLC, (XBridge column; eluents 50 mM ammonium carbonate buffer at pH 10 and methanol) giving the title product as a yellow solid (26.3 mg). LCMS System A: Rt 1.87 m/z [M+H]+ 394.1, System B: Rt 2.57.

후처리

  1. stirringthe mixture was stirred at rt overnight
  2. stirringstirring
  3. waitwas continued at rt for 6 h
  4. stirringthe reaction stirred overnight
  5. stirringstirring
  6. additionwas added in two portions (500 μL and 250 μL)
  7. stirringthe mixture was stirred until rt
  8. extractionThe reaction mixture was extracted with ethyl acetate (3× reaction volume)
  9. customThe phases were separated
  10. concentrationthe organic phase concentrated
  11. customto yield a dark yellow viscous oil
  12. customThe crude product was purified by preparative HPLC, (XBridge column; eluents 50 mM ammonium carbonate buffer at pH 10 and methanol)

출처 및 근거

ORD 기록
ord-676a8fa0b07a4bb08fa85ee410db8c0a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221761B2

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