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Toluene → 1-(3-Chlorophenyl)-3-(1-benzyl-2-pyrrolidinylidene)-2(1H,3H)-indolone

HRID 1110862
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인쇄 미리보기

반응식

HRID 1110862 반응식
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.O=P(Cl)(Cl)Cl.[Cl:26][C:27]1[CH:28]=[C:29]([N:33]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:35][C:34]2=[O:42])[CH:30]=[CH:31][CH:32]=1>C(Cl)Cl>[Cl:26][C:27]1[CH:28]=[C:29]([N:33]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:35](=[C:9]3[CH2:10][CH2:11][CH2:12][N:8]3[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:34]2=[O:42])[CH:30]=[CH:31][CH:32]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1140Toluene2회HCID 24813Phosphorus oxychlorideHCID 791761-Benzyl-3-pyrrolidoneHCID 112995301-(3-Chlorophenyl)-indolin-2-one

생성물 1

HCID 537944421-(3-Chlorophenyl)-3-(1-benzyl-2-pyrrolidinylidene)-2(1H,3H)-indolone

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

N-benzyl-2-pyrrolidone (1.58 ml, 9.85 mmoles) was combined with 2 ml toluene under N2 and cooled to 0°-5°. POCl3 (0.5 ml, 5.9 mmoles) was added and the mixture stirred 30 minutes. Toluene (3 ml) and 1-(3-chloro- phenyl-2(1H,3H)-indolone (1.2 g, 4.92 mmoles) were added and the stirred reaction mixture warmed to 25° for 30 minutes and then to 70°-75° for 18 hours. The reaction mixture was cooled, diluted with 100 ml CH2Cl2, washed with saturated NaHCO3, H2O and brine, dried and concentrated in vacuo to an oil (2.6 g). The oil was chromatographed on silica gel (45×150 mm) using CH2Cl2 as eluant, yielding title product, initially an oil which was crystallized from ether/pentane, 1.04 g (53%), m.p. 72°-75°.

후처리

  1. temperaturecooled to 0°-5°
  2. customthe stirred reaction mixture
  3. temperaturewarmed to 25° for 30 minutes
  4. waitto 70°-75° for 18 hours
  5. temperatureThe reaction mixture was cooled
  6. washwashed with saturated NaHCO3, H2O and brine
  7. customdried
  8. concentrationconcentrated in vacuo to an oil (2.6 g)
  9. customThe oil was chromatographed on silica gel (45×150 mm)

출처 및 근거

ORD 기록
ord-563af21d5ab64430b657afbf771a5fec
출처 데이터셋
uspto-grants-1990_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04977178

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