2-Furanmethanethiol → 2,3-dimethyl-4-(2-furylmethylthio)pyridine N-oxide

HRID 1081682Notes

Reaction equation

HRID 1081682 reaction equation
[OH-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][SH:9].Cl[C:11]1[CH:16]=[CH:15][N+:14]([O-:17])=[C:13]([CH3:18])[C:12]=1[CH3:19]>O1CCOCC1.O>[CH3:18][C:13]1[C:12]([CH3:19])=[C:11]([S:9][CH2:8][C:4]2[O:3][CH:7]=[CH:6][CH:5]=2)[CH:16]=[CH:15][N+:14]=1[O-:17]

Participants

6

Reactant 3

HCID 73632-FuranmethanethiolHCID 14798Sodium HydroxideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

Product 1

HCID 224607942,3-dimethyl-4-(2-furylmethylthio)pyridine N-oxide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

6 g of (60%) NaOH are added in portions to 50 ml of dry dioxane, the mixture is stirred for 15 minutes, 11.7 g (0.11 mol) of 2-furylmethylmercaptan are metered in, in the course of 20 minutes, and the mixture is again stirred for 30 minutes until the evolution of gas has ceased. A solution of 14.4 g (0.1 mol) of 4-chloro-2,3-dimethylpyridine N-oxide in 100 ml of dioxane is subsequently added dropwise in the course of 20 minutes, the reaction mixture is stirred at RT for 1 h, subsequently at 70° C. for 1 h and thereupon at 100° C. for a further 1 h. After the reaction has ended, the mixture is allowed to cool, diluted with 500 ml of water and extracted 4 times using in each case 300 ml of ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulfate, concentrated and crystallized by adding diisopropyl ether. This gives 18.8 g (80% of theory) of 2,3-dimethyl-4-(2-furylmethylthio)pyridine N-oxide of m.p. 111°-112° C.

Workup

  1. customin the course of 20 minutes
  2. stirringthe mixture is again stirred for 30 minutes until the evolution of gas
  3. stirringthe reaction mixture is stirred at RT for 1 h, subsequently at 70° C. for 1 h
  4. waitat 100° C. for a further 1 h
  5. temperatureto cool
  6. extractionextracted 4 times
  7. washThe combined organic phases are washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customcrystallized
  11. additionby adding diisopropyl ether

Sources & evidence

ORD record
ord-7146856143cb4ec28cc0d0ff203c381e
Source dataset
uspto-grants-1996_12
Patent number
US05587389

Reaction notes

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