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

HRID 1110862
ノート
印刷プレビュー

反応式

HRID 1110862 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1140Toluene2 回HCID 24813Phosphorus oxychlorideHCID 791761-Benzyl-3-pyrrolidoneHCID 112995301-(3-Chlorophenyl)-indolin-2-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

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°.

後処理

  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)

出典と根拠

ORDレコード
ord-563af21d5ab64430b657afbf771a5fec
出典データセット
uspto-grants-1990_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04977178

反応ノート

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