Hydantoin → 3-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxybenzylidene-2,4-imidazolidinedione

HRID 1765427노트

반응식

HRID 1765427 반응식
[NH:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].N1CCCC1.[CH3:13][C:14]1[C:15]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])[CH:31]=O)=[CH:16][C:17]2[C:18]([CH3:27])([CH3:26])[CH2:19][CH2:20][C:21]([CH3:25])([CH3:24])[C:22]=2[CH:23]=1>C(O)C>[CH3:13][C:14]1[C:15]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])[CH:31]=[C:5]2[NH:1][C:2](=[O:7])[NH:3][C:4]2=[O:6])=[CH:16][C:17]2[C:18]([CH3:27])([CH3:26])[CH2:19][CH2:20][C:21]([CH3:24])([CH3:25])[C:22]=2[CH:23]=1

참가 물질

5

반응물 3

HCID 10006HydantoinHCID 31268PyrrolidineHCID 112791263-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4-methoxy-benzaldehyde

생성물 1

HCID 694623563-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxybenzylidene-2,4-imidazolidinedione

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2,4-imidazolidinedione (101 mg, 1.0 mmol), pyrrolidine (0.04 mL, 0.5 mmol) and 3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4-methoxy-benzaldehyde (336 mg, 1.0 mmol) in ethanol (15 mL) was heated under reflux for 24 hours, allowed to cool to room temperature and extracted with ethyl acetate (2×100 mL). The organic extracts were washed with saturated aqueous NH4Cl (60 mL), saturated NH4Cl (70 mL), saturated aqueous NaCl (60 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave a yellow solid that was purified by column chromatography, using a Biotage 40S cartridge, eluting with ethyl acetate/hexane (3:7). The title compound was isolated as a yellow solid (270 mg, 65%).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe organic extracts were washed with saturated aqueous NH4Cl (60 mL), saturated NH4Cl (70 mL), saturated aqueous NaCl (60 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customRemoval of the solvent under reduced pressure
  8. customgave a yellow solid
  9. customthat was purified by column chromatography
  10. washeluting with ethyl acetate/hexane (3:7)

출처 및 근거

ORD 기록
ord-21c2d7d93983460c8cb2bd0b5c56ea77
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07226940B2

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