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1H-Isoindole-1,3(2H)-dione, 2-(3-amino-4-chlorophenyl)- → Isopentyl 2-[(2-Chloro-5-phthalimidophenyl)amino]propionate

HRID 1939139
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HRID 1939139 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH:21]([CH3:30])[C:22]([O:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])=[CH:3][C:2]=1[NH:1][CH:21]([CH3:30])[C:22]([O:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23]
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참가 물질

5

반응물 3

HCID 3338121H-Isoindole-1,3(2H)-dione, 2-(3-amino-4-chlorophenyl)-HCID 516892Sodium BicarbonateHCID 522863Isopentyl 2-bromopropanoate

생성물 1

HCID 21467014Isopentyl 2-[(2-Chloro-5-phthalimidophenyl)amino]propionate수율 65.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

A mixture of 1.64 g of N-(3-amino-4-chlorophenyl)phthalimide, 2.68 g of isopentyl 2-bromopropionate, and 0.60 g of sodium hydrogencarbonate was heated at 150° C. for 5 hours while stirring. While the reaction mixture was hot, ethyl acetate was added thereto, and the reaction mixture was washed successively with water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:8) to give 1.63 g of the title compound (Table 1, Compound No. 5).

후처리

  1. washthe reaction mixture was washed successively with water
  2. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:8)

출처 및 근거

ORD 기록
ord-4525023e361d4c5783a70d8ef30c3b67
출처 데이터셋
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05696056

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