Water → HCID 86676043, compound

HRID 1502184Notes

Reaction equation

HRID 1502184 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:26]4[CH:31]=[CH:30][C:29](CCCCCCCCBr)=[CH:28][CH:27]=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.[C:41]([O-:44])(=[S:43])[CH3:42].[K+].[OH2:46]>O1CCCC1.C(O)C>[C:41]([O:44][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:7][CH2:19][CH2:18][O:46][C:29]1[CH:30]=[CH:31][C:26]([N:11]2[C:12]3[CH:13]=[CH:14][C:15]([C:20]4[S:21][C:22]([CH3:25])=[CH:23][CH:24]=4)=[CH:16][C:17]=3[C:18]3[C:10]2=[CH:9][CH:8]=[C:7]([C:5]2[S:6][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:19]=3)=[CH:27][CH:28]=1)(=[S:43])[CH3:42]

Participants

6

Reactant 3

HCID 962WaterHCID 23670855Potassium ethanethioateHCID 86676044HCID 86676044, compound

Product 1

HCID 86676043HCID 86676043, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The obtained 3,6-bis(5-methylthiophen-2-yl)-9-[4-(8-bromooctyl)phenyl]carbazole (1.50 g, 2.3 mmol) was dissolved in a solvent mixture of tetrahydrofuran (THF) (20 mL) and ethanol (20 mL). Under nitrogen flow, potassium thioacetate (0.40 g, 3.5 mmol) was added to the resultant solution, and the mixture was refluxed for 5 hours and left to cool to room temperature. Next, the resultant mixture was poured to water, followed by extraction with methylene chloride. In addition, the mixture was washed with water and dried and the solvent was evaporated, to thereby a pale yellowish-white solid. The obtained solid was purified through silica gel column chromatography using as an eluent a solvent mixture of methylene chloride/hexane (13/7 by volume), to thereby obtain 1.22 g of 8-{4-[3,6-bis(5-methylthiophen-2-yl)carbazol-9-yl]phenoxy}octyl thioacetate.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. waitleft
  3. extractionfollowed by extraction with methylene chloride
  4. washIn addition, the mixture was washed with water
  5. customdried
  6. customthe solvent was evaporated
  7. customThe obtained solid was purified through silica gel column chromatography
  8. additiona solvent mixture of methylene chloride/hexane (13/7 by volume)

Sources & evidence

ORD record
ord-6449a9b2d75b4605bebe39a217b76da5
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Reaction notes

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