Water → HCID 86676046, compound

HRID 1502188Notes

Reaction equation

HRID 1502188 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:26]4[CH:51]=[CH:50][C:29]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]OS(C5C=CC(C)=CC=5)(=O)=O)=[CH:28][CH:27]=4)[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:52]([O-:55])(=[S:54])[CH3:53].[K+].O>O1CCCC1.C(O)C>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:26]4[CH:27]=[CH:28][C:29]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:55][C:52](=[S:54])[CH3:53])=[CH:50][CH:51]=4)[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23670855Potassium ethanethioateHCID 86676045HCID 86676045, compound

Product 1

HCID 86676046HCID 86676046, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The obtained toluene-4-sulfonic acid 8-[4-(3,6-diphenylcarbazol-9-yl)phenoxy]octyl ester (1.90 g, 2.7 mmol) was dissolved in a solvent mixture of tetrahydrofuran (THF) (40 mL) and ethanol (20 mL). Under nitrogen flow, potassium thioacetate (0.55 g, 4.8 mmol) was added to the resultant solution, and the mixture was refluxed for 7 hours and left to cool to room temperature. Next, the mixture was poured to water, followed by extraction with ethyl acetate. In addition, the mixture was washed with water and dried and the solvent was evaporated, to thereby obtain a crude product. The crude product was purified through silica gel column chromatography using toluene an eluent, to thereby obtain 1.32 g of thioacetic acid 8-[4-(3,6-diphenylcarbazol-9-yl)phenoxy]octyl ester as pale orange oily matter.

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. waitleft
  3. extractionfollowed by extraction with ethyl acetate
  4. washIn addition, the mixture was washed with water
  5. customdried
  6. customthe solvent was evaporated
  7. customto thereby obtain a crude product
  8. customThe crude product was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-0622969ffbc94f6bb632fde8e32fd836
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Reaction notes

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