Diethyl sulfoxide → 9,9-Bis(4-pyridinylmethyl)thioxanthene

HRID 1648140Notes

Reaction equation

HRID 1648140 reaction equation
[H-].[Na+].C(S(CC)=O)C.[N:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[S:23][C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:11][CH:10]=1.[N:30]1[CH:35]=[CH:34][C:33]([CH2:36]Cl)=[CH:32][CH:31]=1>CS(C)=O>[N:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]2([CH2:36][C:33]3[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=3)[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[S:23][C:24]3[C:29]2=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6263Diethyl sulfoxideHCID 24758Sodium hydrideHCID 745714-(Chloromethyl)pyridineHCID 199224849-(4-Pyridinylmethyl)thioxanthene

Product 1

HCID 149415699,9-Bis(4-pyridinylmethyl)thioxantheneYield 65.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A quantity of 0.38 g (8.0 mmole) of 50% sodium hydride oil dispersion was added slowly during 15 minutes to 20 ml of ethyl sulfoxide at room temperature. After completion of addition, the reaction mixture was heated at 45° for 30 minutes. It was cooled to 15° and a solution of 2.3 g (8.0 mmole) of 9-(4-pyridinylmethyl)thioxanthene in 10 ml of dimethylsulfoxide was added dropwise during 15 minutes at room temperature. After completion of addition, the reaction mixture was stirred 30 minutes at room temperature. Then a solution of 4-picolylchloride (8.75 mmole) in 5 ml of dimethylsulfoxide was added dropwise during 30 minutes at ambient temperature. The reaction was then heated at 40° for 30 minutes. The reaction was quenched by addition of water (50 ml). Trituration of the precipitated oil yielded a crystalline solid, which was filtered off, washed with water and dried. The tan solid was dissolved in benzene and decolorized by stirring with 1 g of Magnesol® for 30 minutes. Filtration and evaporation yielded a colorless product (2.0 g) which was recrystallized from ethylacetate, m.p., 201.4°-203.4°.

Workup

  1. additionAfter completion of addition
  2. temperaturethe reaction mixture was heated at 45° for 30 minutes
  3. temperatureIt was cooled to 15°
  4. additionAfter completion of addition
  5. temperatureThe reaction was then heated at 40° for 30 minutes
  6. customThe reaction was quenched by addition of water (50 ml)
  7. customTrituration of the precipitated oil yielded a crystalline solid, which
  8. filtrationwas filtered off
  9. washwashed with water
  10. customdried
  11. dissolutionThe tan solid was dissolved in benzene
  12. stirringby stirring with 1 g of Magnesol® for 30 minutes
  13. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-80b58cb8e1004b49aa2f6969f0a91b97
Source dataset
uspto-grants-1995_07
Patent number
US05434264

Reaction notes

Loading…