Sulfuric Acid → 5,11-Dihydroindolo[3,2-b]carbazole

HRID 1455854ノート

反応式

HRID 1455854 の反応式
S(=O)(=O)(O)O.[C:6]1([N:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)N=C2CCC(=O)CC2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)(=O)C>[CH:8]1[CH:9]=[CH:10][CH:11]=[C:6]2[NH:12][C:24]3[C:25](=[CH:26][C:21]4[NH:12][C:6]5[C:7]([C:22]=4[CH:23]=3)=[CH:8][CH:9]=[CH:10][CH:11]=5)[C:7]=12

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 22105110Cyclohexane-1,4-dione bisphenylhydrazone

生成物 1

HCID 958385,11-Dihydroindolo[3,2-b]carbazole収率 71.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
10 °C

実験手順

In a 1.5 liter flask equipped with a mechanical stirrer and a condenser were added glacial acetic acid (100 milliliters) and concentrated sulfuric acid (20 milliliters). Into this mixture, which was maintained at 10° C. with an ice bath, was added powdered cyclohexane-1,4-dione bisphenylhydrazone (22.0 grams) in small portions with stirring. After the aforementioned addition, the ice bath was removed and the mixture was allowed to warm to 23° C., and stirred for a further 10 minutes. Subsequently, the mixture was heated to about 65° C. (Centigrade throughout) until an exothermic reaction occurred. The reaction mixture was cooled with an ice bath, and within 5 minutes a light brown solid was formed. The reaction mixture was allowed to remain at room temperature, about 25° C., for about 18 hours, and filtered. The filtered cake was then washed with acetic acid, water, and then stirred in boiling methanol for 30 minutes before filtering and drying in vacuo for about 2 to 5 hours to provide 7.2 grams of pure 5,11-dihydroindolo[3,2-b]carbazole as pale yellow crystals.

後処理

  1. customIn a 1.5 liter flask equipped with a mechanical stirrer and a condenser
  2. additionAfter the aforementioned addition
  3. customthe ice bath was removed
  4. temperatureto warm to 23° C.
  5. stirringstirred for a further 10 minutes
  6. temperatureSubsequently, the mixture was heated to about 65° C. (Centigrade throughout)
  7. customuntil an exothermic reaction
  8. temperatureThe reaction mixture was cooled with an ice bath
  9. customwithin 5 minutes a light brown solid was formed
  10. filtrationfiltered
  11. washThe filtered cake was then washed with acetic acid, water
  12. stirringstirred
  13. customfor 30 minutes
  14. filtrationbefore filtering
  15. customdrying in vacuo for about 2 to 5 hours

出典と根拠

ORDレコード
ord-5efbaddd46c34f42ac61b93560ee3b5d
出典データセット
uspto-grants-1998_12
特許番号
US05843607

反応ノート

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