Potassium Carbonate → 5,11-Di-m-tolyl-5,11-dihydroindolo[3,2-b]carbazole

HRID 1455855

반응식

HRID 1455855 반응식
[CH:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[NH:7][C:8]3[C:9](=[CH:10][C:11]4[NH:12][C:13]5[C:18]([C:19]=4[CH:20]=3)=[CH:17][CH:16]=[CH:15][CH:14]=5)[C:2]=12.I[C:22]1[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].CCCCCC[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O.C1(C)C=CC=CC=1>[C:24]1([CH3:28])[CH:25]=[CH:26][CH:27]=[C:22]([N:12]2[C:11]3[C:19](=[CH:20][C:8]4[N:7]([C:46]5[CH:47]=[C:42]([CH3:41])[CH:43]=[CH:44][CH:45]=5)[C:3]5[C:2]([C:9]=4[CH:10]=3)=[CH:1][CH:6]=[CH:5][CH:4]=5)[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:23]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 122683-IodotolueneHCID 12388TridecaneHCID 958385,11-Dihydroindolo[3,2-b]carbazole

생성물 1

HCID 154049595,11-Di-m-tolyl-5,11-dihydroindolo[3,2-b]carbazole

시약·촉매·용매 3

HCID 24463Copper sulfate pentahydrate촉매HCID 962Water용매HCID 1140Toluene용매

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온도
250 °C

실험 절차

A 200-milliliter 3-necked round bottom flask equipped with a mechanical stirrer, reflux condenser, and argon inlet was purged with argon and then charged with 5,11-dihydroindolo[3,2-b]carbazole (5.1 grams, 0.02 mol), 3-iodotoluene (8.69 grams, 0.04 mol), copper sulfate pentahydrate (0.25 gram, 1.0 mmol), potassium carbonate (5.52 grams, 0.04 mol), and n-tridecane (5.0 milliliters). Under an argon atmosphere, the reaction mixture was heated to about 250° C. with a heating mantle and allowed to proceed at this temperature to completion in about 6 hours. The mixture was cooled to about 100° C., and 100 milliliters of toluene and 15 milliliters of water were then added with vigorous stirring. The resulting two phase mixture was transferred into a separatory funnel and the layers separated. The organic phase, which contained the desired product, was washed with water, and treated with 25 grams of alumina under an argon atmosphere, and filtered. The filtrate was then evaporated and the residue was recrystallized from cyclohexane to provide 6.8 grams of pure, about 99.9 percent, 5,11-di-m-tolyl-5,11-dihydroindolo-[3,2-b]carbazole (1).

후처리

  1. customA 200-milliliter 3-necked round bottom flask equipped with a mechanical stirrer
  2. temperaturereflux condenser, and argon inlet
  3. customwas purged with argon
  4. temperatureThe mixture was cooled to about 100° C.
  5. customThe resulting two phase mixture was transferred into a separatory funnel
  6. customthe layers separated
  7. washwas washed with water
  8. additiontreated with 25 grams of alumina under an argon atmosphere
  9. filtrationfiltered
  10. customThe filtrate was then evaporated
  11. customthe residue was recrystallized from cyclohexane

출처 및 근거

ORD 기록
ord-4719ee4de4624803a19d4699cd571b1f
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843607

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