Sodium Hydroxide → 5,6-Dichloro-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)-1H-isoindole-1,3(2H)-dione

HRID 272318노트

반응식

HRID 272318 반응식
[CH3:1][C:2]1([CH3:21])[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5]2[C:13]([CH3:20])=[C:14]([NH2:19])[C:15]([CH3:18])=[C:16]([CH3:17])[C:4]=2[O:3]1.[Cl:22][C:23]1[CH:24]=[C:25]2[C:30](=O)[O:29][C:27](=[O:28])[C:26]2=[CH:32][C:33]=1[Cl:34].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[OH-].[Na+]>O1CCCC1.O>[Cl:22][C:23]1[CH:24]=[C:25]2[C:26](=[CH:32][C:33]=1[Cl:34])[C:27](=[O:28])[N:19]([C:14]1[C:15]([CH3:18])=[C:16]([CH3:17])[C:4]3[O:3][C:2]([CH3:21])([CH3:1])[CH:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:5]=3[C:13]=1[CH3:20])[C:30]2=[O:29]

참가 물질

8

반응물 5

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 703344,5-Dichlorophthalic anhydrideHCID 757711-HydroxybenzotriazoleHCID 105407985-Amino-2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydrobenzofuran

생성물 1

HCID 219613375,6-Dichloro-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)-1H-isoindole-1,3(2H)-dione수율 68%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-amine (1.00 g, 3.56 mmol) in tetrahydrofuran (30 ml) was added under an argon atmosphere 4,5-dichlorophthalic anhydride (850.6 mg, 3.92 mmol) and the mixture was refluxed with heating for 13 hours. The reaction mixture was cooled down to room temperature and then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (WSC) hydrochloride (760.0 mg, 3.96 mmol) and 1-hydroxy-1H-benzotriazole (HOBT) monohydrate (602.6 mg, 3.93 mmol) were added to the mixture. The resulting mixture was refluxed with heating for 3 hours and then cooled down to room temperature. Water and an 8 N aqueous solution of sodium hydroxide were added into the reaction mixture and 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 (68% yield) of the title compound. Melting point: 178-181° C.

후처리

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 13 hours
  3. temperatureThe resulting mixture was refluxed
  4. temperaturewith heating for 3 hours
  5. temperaturecooled down to room temperature
  6. extractionthe product was extracted twice with ethyl acetate
  7. washThe combined extracts were washed with an aqueous, saturated solution of sodium hydrogen carbonate
  8. customdried on magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-3c3379276a084e3c8f260091420ee637
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456162B2

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