Water → HCID 17855564, compound

HRID 732282Notes

Reaction equation

HRID 732282 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O>C(#N)C>[CH:5]1[C:6]([C:10]#[N:11])=[CH:7][CH:8]=[C:9]2[C:4]=1[C:3]1[C:2]([NH:1]2)=[C:2]2[NH:1][C:9]3[CH:8]=[CH:7][C:6]([C:10]#[N:11])=[CH:5][C:4]=3[C:3]2=[C:2]2[NH:1][C:9]3[CH:8]=[CH:7][C:6]([C:10]#[N:11])=[CH:5][C:4]=3[C:3]=12

Participants

4

Reactant 2

HCID 962WaterHCID 27513Indole-5-carbonitrile2×

Product 1

HCID 17855564HCID 17855564, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

10 ml of acetonitrile was poured into a 200 ml three-neck flask, and 1.42 g of indole-5-carbonitrile was dissolved therein. On the other hand, an oxidant solution was prepared by dissolving 16.2 g of ferric chloride anhydrate and 5.4 g of water in 40 ml of acetonitrile and agitating the resultant mixture for 10 minutes. Then the prepared oxidant solution was dripped into the indole-5-carbonitrile solution for 30 minutes, which was then agitated for 10 hours at the temperature of 60° C. Color of the reaction solution changed from yellow to green with slight heat generation, and the pH was less than 1. After the end of the reaction, the reaction solution was suction-filtered with a perforated funnel, and the filtrate was washed with acetonitrile and then methanol, and then dried to obtain 1.22 g of 6,11-dihydro-5H-diindolo[2,3-a:2′,3′-c] carbazole-2,9,14-tricarbonitrile (indole-5-carbonitrile trimer) with a green color (yield: 86%). The resultant trimer was pressure-molded with a tablet molding machine and the mold was cut into a piece with the diameter of 10 mm and thickness of 1 mm. A conductivity thereof was measured by the four terminal method and found to be 0.50 S/cm. The result of elemental analysis was: <C9.00H4.03N1.97Cl0.10>3. Further the result of X-ray diffraction crystal analysis indicated that the interlaminar spacing was 0.44 nm.

Workup

  1. customOn the other hand, an oxidant solution was prepared
  2. customAfter the end of the reaction
  3. filtrationthe reaction solution was suction-filtered with a perforated funnel
  4. washthe filtrate was washed with acetonitrile
  5. dry with materialmethanol, and then dried

Sources & evidence

ORD record
ord-7a1ebc05b6ae4461a583267f4d8de18a
Source dataset
uspto-grants-2009_09
Patent number
US07585981B2

Reaction notes

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