Sodium hydride → 9,9-Bis(4-pyridinylmethyl)thioxanthene

HRID 1463668Notes

Reaction equation

HRID 1463668 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:17][C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:5][CH:4]=1.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][CH:25]=1>CS(C)=O>[N:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]2([CH2:30][C:27]3[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[S:17][C:18]3[C:23]2=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 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 SulfoxideSolvent3×

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 dimethyl 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-786bb7805bc6456ca8a4e52304135722
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

Loading…