تفاعل #1543037

ord-4719ee4de4624803a19d4699cd571b1f

معادلة التفاعل

c1ccc2c(c1)[nH]c1cc3c(cc12)[nH]c1ccccc13
5,11-dihydroindolo[3,2-b]carbazole
Cc1cccc(I)c1
3-iodotoluene
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCCCCCCCCCCCC
n-tridecane
Cc1cccc(-n2c3ccccc3c3cc4c(cc32)c2ccccc2n4-c2cccc(C)c2)c1
5,11-di-m-tolyl-5,11-dihydroindolo-[3,2-b]carbazole
Cc1cccc(-n2c3ccccc3c3cc4c(cc32)c2ccccc2n4-c2cccc(C)c2)c1
5,11-di-m-tolyl-5,11-dihydroindolo[3,2-b]carbazole

المذيبات

ظروف التفاعل

درجة الحرارة
250°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىA 200-milliliter 3-necked round bottom flask equipped with a mechanical stirrer
  2. 2
    درجة الحرارةreflux condenser, and argon inlet
  3. 3
    أخرىwas purged with argon
  4. 4
    درجة الحرارةThe mixture was cooled to about 100° C.
  5. 5
    أخرىThe resulting two phase mixture was transferred into a separatory funnel
  6. 6
    أخرىthe layers separated
  7. 7
    غسيلwas washed with water
  8. 8
    workup.ADDITIONtreated with 25 grams of alumina under an argon atmosphere
  9. 9
    ترشيحfiltered
  10. 10
    أخرىThe filtrate was then evaporated
  11. 11
    أخرىthe residue was recrystallized from cyclohexane

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05843607uspto-grants-1998_12