Water → HCID 13457715, 화합물

HRID 280114

반응식

HRID 280114 반응식
[C:1]1(=[O:16])[N:5]([N:6]2[CH:10]=[CH:9][CH:8]=[CH:7]2)[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]12.[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].O>ClC(Cl)C>[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([C:7]1[N:6]([N:5]2[C:4](=[O:11])[C:3]3=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]3[C:1]2=[O:16])[CH:10]=[CH:9][CH:8]=1)=[O:21]

참가 물질

5

반응물 3

HCID 962WaterHCID 98082-Fluorobenzoyl chlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

생성물 1

HCID 13457715HCID 13457715, 화합물수율 19.1%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a mixture of N-phthalimidopyrrole (10 g, 47 mmole) and fused zinc chloride (10 g, 73 mmole) in 80 ml dichloroethane was added o-fluorobenzoyl chloride (7.5 g, 47 mmole). The reaction mixture was stirred at ambient temperature for twenty hours and at 80° for one hour. Thereafter, it was cooled, poured into water and extracted with dichloromethane. The organic extract was washed with water and with saturated sodium chloride solution, and dried over magnesium sulfate. The solution was filtered and evaporated to an oil which yielded a solid upon trituration with ethanol (yield 11 g, m.p. 180°-190°). This material was purified by column chromatography (silica gel, dichloromethane) to give 3 g solid. This material was recrystallized from isopropanol to give 2.6 g (17%) crystals, m.p. 202°-203°.

후처리

  1. temperatureThereafter, it was cooled
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water and with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe solution was filtered
  7. customevaporated to an oil which
  8. customyielded a solid upon trituration with ethanol (yield 11 g, m.p. 180°-190°)
  9. customThis material was purified by column chromatography (silica gel, dichloromethane)

출처 및 근거

ORD 기록
ord-f2380600dd884d9aaa5ae237f813d429
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588727

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