Water → HCID 87123700, compound

HRID 1639486Notes

Reaction equation

HRID 1639486 reaction equation
[I-:1].C([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([S+:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]3[CH:23]=[CH:24][CH:25]=[CH:26][C:15]2=3)=[CH:10][CH:9]=1)(=O)C.[OH-].C[N+](C)(C)C.O.C(Cl)(Cl)Cl>CO>[I-:1].[OH:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([S+:14]2[C:15]3[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]2=3)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 60966Tetramethylammonium hydroxideHCID 87123706HCID 87123706, compound

Product 1

HCID 87123700HCID 87123700, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

While cooling with ice, 10.0 g of dibenzothiophene-S-oxide synthesized in the above step (1) is added to 30 g of diphosphorus pentoxide/methanesulfonic acid (9/1), and further 10 ml of 2-phenylethyl acetate is added thereto. The reaction solution is stirred at room temperature for 6 hours, and then poured into ice water. The obtained aqueous solution is filtered, and 23 g of potassium iodide is added. Crystals precipitated are recovered by filtration to obtain 11.1 g of 5-[(4-(2-acetoxyethyl)-phenyl]dibenzothiophenium iodide. The obtained 11.1 g of 5-[4-(2-acetoxyethyl)-phenyl]dibenzothiophenium iodide is dissolved in 200 ml of methanol, 10.7 g of a 20% aqueous solution of tetramethylammonium hydroxide is added to the solution, followed by stirring at room temperature for 2 hours. Subsequently, 100 ml of ion exchange water and 100 ml of chloroform are added to the solution to extract a chloroform layer. After the solvent is distilled off under reduced pressure, the reaction product is washed with ethyl acetate to obtain 8.5 g of the aiming 5-[4-(2-hydroxyethyl)phenyl]dibenzothiophenium iodide.

Workup

  1. extractionto extract a chloroform layer
  2. distillationAfter the solvent is distilled off under reduced pressure
  3. washthe reaction product is washed with ethyl acetate

Sources & evidence

ORD record
ord-9ea8312f4e3e4424872cd4ef209f6a30
Source dataset
uspto-grants-2012_02
Patent number
US08110333B2

Reaction notes

Loading…