Sodium methanesulfinate → HCID 12807911, compound

HRID 543698Notes

Reaction equation

HRID 543698 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:12]Cl.[CH3:14][S:15]([O-:17])=[O:16].[Na+]>CN(C)C=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:12][S:15]([CH3:14])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 20460498HCID 20460498, compound

Product 1

HCID 12807911HCID 12807911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-3-chloromethylquinoline (14.2 g.) was added to a stirred suspension of sodium methanesulphinate (7.3 g.) in dimethylformamide (150 ml.) at room temperature. The mixture was stirred for 14 hours at room temperature, then for 0.5 hour at 95°-100°. The solvent was evaporated to half volume and water added to the residue. The resulting solid product was collected and dissolved in dichloromethane. The solution was dried, filtered from charcoal, and evaporated. The resulting solid was triturated with petroleum ether to give the novel compound 4-chloro-3-methylsulphonylmethylquinoline, m.p. 202°-204°.

Workup

  1. waitfor 0.5 hour at 95°-100°
  2. customThe solvent was evaporated to half volume and water
  3. additionadded to the residue
  4. customThe resulting solid product was collected
  5. dissolutiondissolved in dichloromethane
  6. customThe solution was dried
  7. filtrationfiltered from charcoal
  8. customevaporated
  9. customThe resulting solid was triturated with petroleum ether

Sources & evidence

ORD record
ord-3702faf4dce9437abad31d7c02d61306
Source dataset
uspto-grants-1984_05
Patent number
US04447435

Reaction notes

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