4,4'-Bis(dimethylamino)benzophenone → 6,6-Bis(p-dimethylaminophenyl)-6,11-dihydro-[1]benzopyrano[4,3-b]indole

HRID 27003

反応式

HRID 27003 の反応式
[CH3:1][N:2]([CH3:20])[C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O.O[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[NH:34][C:35]2[C:40]([CH:41]=1)=[CH:39][CH:38]=[CH:37][CH:36]=2.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:17][N:15]([CH3:16])[C:12]1[CH:13]=[CH:14][C:9]([C:7]2([C:6]3[CH:5]=[CH:4][C:3]([N:2]([CH3:20])[CH3:1])=[CH:19][CH:18]=3)[C:41]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[NH:34][C:33]=3[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[O:8]2)=[CH:10][CH:11]=1

参加物

6

反応物 4

HCID 70314,4'-Bis(dimethylamino)benzophenoneHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 7000092-(1H-indol-2-yl)phenol

生成物 1

HCID 126326916,6-Bis(p-dimethylaminophenyl)-6,11-dihydro-[1]benzopyrano[4,3-b]indole収率 30.4%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒3 回

実験手順

7.7 g of 4,4'-bisdimethylaminobenzophenone was dissolved in 50 ml of chloroform, and the solution was stirred. Phosphorus oxychloride (5 g) and 10 ml of chloroform were added thereto, and the mixture was stirred for 30 minutes at room temperature (about 20°-30° C.). Then, 6 g of 2-(2'-hydroxyphenyl)indole was added thereto, and the mixture was stirred at room temperature for 3 hours. The mixture was heated under reflux for an additional 2 hours. The heated mixture was cooled to room temperature, and poured into ice water, and neutralized with an aqueous solution of sodium hydroxide. Furthermore, 200 to 300 ml of chloroform was added for extraction. The chloroform layer was washed with water, dried, and distilled under reduced pressure to remove the chloroform. The remaining oily substance was dissolved in a small amount of methanol by heating, and the solution was cooled. The crystals precipitated were separated by filtration, and dried to obtain 4 g of the objective compound having a melting point of 165° to 168° C.

後処理

  1. stirringthe mixture was stirred for 30 minutes at room temperature (about 20°-30° C.)
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for an additional 2 hours
  5. washThe chloroform layer was washed with water
  6. customdried
  7. distillationdistilled under reduced pressure
  8. customto remove the chloroform
  9. dissolutionThe remaining oily substance was dissolved in a small amount of methanol
  10. temperatureby heating
  11. temperaturethe solution was cooled
  12. customThe crystals precipitated
  13. customwere separated by filtration
  14. customdried

出典と根拠

ORDレコード
ord-f245225b407842029f8a857b573e11cc
出典データセット
uspto-grants-1980_09
特許番号
US04220356

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