Potassium Carbonate → HCID 66717046, compound

HRID 1502182Notes

Reaction equation

HRID 1502182 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[NH:11][C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][C:15]([C:20]2[S:21][C:22]([CH3:25])=[CH:23][CH:24]=2)=[CH:14][CH:13]=4)=[CH:4][CH:3]=1.I[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].C1(C)C=CC=CC=1>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][C:15]([C:20]2[S:21][C:22]([CH3:25])=[CH:23][CH:24]=2)=[CH:14][CH:13]=4)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 696764-IodoanisoleHCID 66716960HCID 66716960, compound

Product 1

HCID 66717046HCID 66717046, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The obtained 3,6-bis(5-methylthiophen-2-yl)carbazole (8.07 g, 22.4 mmol), 4-iodoanisole (21.00 g, 89.7 mmol), copper powder (0.71 g) and potassium carbonate (12.40 g) were mixed together. The mixture was refluxed in a nitrogen atmosphere for 6 hours and cooled to 100° C. Next, toluene (80 mL) was added thereto, and the resultant mixture was filtrated using a filtration aid to remove insoluble matter. Thereafter, the solvent was evaporated under reduced pressure. The residue was dissolved in methylene chloride, and the solution was washed with water and dried to obtain a brown liquid. Next, the obtained liquid was purified through silica gel column chromatography using as an eluent a solvent mixture of methylene chloride/hexane (3/7 by volume), to thereby obtain 4.39 g of 3,6-bis(5-methylthiophen-2-yl)-9-(4-methoxyphenyl)carbazole.

Workup

  1. temperatureThe mixture was refluxed in a nitrogen atmosphere for 6 hours
  2. filtrationthe resultant mixture was filtrated
  3. customto remove insoluble matter
  4. customThereafter, the solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washthe solution was washed with water
  7. customdried
  8. customto obtain a brown liquid
  9. customNext, the obtained liquid was purified through silica gel column chromatography
  10. additiona solvent mixture of methylene chloride/hexane (3/7 by volume)

Sources & evidence

ORD record
ord-a258a8032a744225a8d8025204f8e009
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Reaction notes

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