Phthalic Anhydride → 2-[2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindole-1,3(2H)-dione

HRID 1017829노트

반응식

HRID 1017829 반응식
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][C:13]1([CH3:33])[CH:17]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[C:16]2[C:25]([CH3:32])=[C:26]([NH2:31])[C:27]([CH3:30])=[C:28]([CH3:29])[C:15]=2[O:14]1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.[OH-].[Na+]>O1CCCC1>[CH3:12][C:13]1([CH3:33])[CH:17]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)[C:16]2[C:25]([CH3:32])=[C:26]([N:31]3[C:1](=[O:11])[C:2]4[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4]3=[O:6])[C:27]([CH3:30])=[C:28]([CH3:29])[C:15]=2[O:14]1

참가 물질

7

반응물 5

HCID 6811Phthalic AnhydrideHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 106853092,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

생성물 1

HCID 219613242-[2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindole-1,3(2H)-dione수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of phthalic anhydride (566.4 mg, 3.82 mmol) in tetrahydrofuran (5 ml) was added a solution of 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine (987.3 mg, 3.38 mmol) in tetrahydrofuran(10 ml) and the resulting mixture was refluxed with heating for 11 hours. The reaction mixture was cooled down to room temperature and then concentrated under reduced pressure. Sodium acetate (314.6 mg, 3.84 mmol) and acetic anhydride (20 ml) were added into the residue and the resulting mixture was stirred at 90° C. for 2 hours. The reaction mixture was cooled down to room temperature and then an 8 N aqueous solution of sodium hydroxide was added into the mixture until it became basic. The product was extracted twice with ethyl acetate. The combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from ethyl acetate to obtain 1.16 g (81% yield) of the title compound. Melting point: 222-224° C.

후처리

  1. temperaturethe resulting mixture was refluxed
  2. temperaturewith heating for 11 hours
  3. concentrationconcentrated under reduced pressure
  4. temperatureThe reaction mixture was cooled down to room temperature
  5. extractionThe product was extracted twice with ethyl acetate
  6. washThe combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate
  7. customdried on magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-477f674e753e401baedb51eabb45c078
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479536B1

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