Hydroquinone → 4,4'-((((4-Methoxyphenyl)azanediyl)bis(ethane-2,1-diyl))bis(oxy))diphenol

HRID 1053595노트

반응식

HRID 1053595 반응식
Cl[CH2:2][CH2:3][N:4]([CH2:13][CH2:14]Cl)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[C:16]([O-:19])([O-])=O.[K+].[K+].[C:22]1([CH:29]=[CH:28][C:26]([OH:27])=[CH:25][CH:24]=1)[OH:23]>CN(C=O)C>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([N:4]([CH2:13][CH2:14][O:11][C:8]2[CH:9]=[CH:10][C:16]([OH:19])=[CH:6][CH:7]=2)[CH2:3][CH2:2][O:23][C:22]2[CH:29]=[CH:28][C:26]([OH:27])=[CH:25][CH:24]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 15064N,N-Bis(2-chloroethyl)-4-methoxybenzenamine

생성물 1

HCID 717360914,4'-((((4-Methoxyphenyl)azanediyl)bis(ethane-2,1-diyl))bis(oxy))diphenol수율 16.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of compound 26a (100 mg, 0.6 mmol), K2CO3 (110 mg, 0.8 mmol), and KI (15 mg, 0.02 mmol) in DMF (50 mL) was bubbled with argon for 10 min. Hydroquinone (220 mg, 2 mmol) was added to the mixture under argon. The reaction mixture was heated and stirred at 80° C. for 6 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mL water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with EtOAc and the combined organic layer was washed with water, then brine, and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/EtOAc (3:1) to provide the compound 26 (20 mg, 0.05 mmol, 13% yield). 1H NMR (CDCl3, 400 MHz) δ 6.82-6.87 (m, 2H), 6.72-6.78 (m, 10H), 4.90 (bs, 2H), 4.07 (t, J=6.0 Hz, 4H), 3.76 (t, J=8.0 Hz, 7H).

후처리

  1. customwas bubbled with argon for 10 min
  2. temperatureThe reaction mixture was heated
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was evaporated
  5. customthe residue was quenched with 100 mL water
  6. extractionThe mixture was then extracted with EtOAc
  7. washthe combined organic layer was washed with water
  8. dry with materialbrine, and dried over Na2SO4
  9. customThe solvent was evaporated
  10. customthe residue was purified by silica gel column chromatography with hexane/EtOAc (3:1)

출처 및 근거

ORD 기록
ord-c06cf6c17c0749cf9e5a2d46983850f5
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394233B2

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