Sodium methanethiolate → 2-Ethyl-5-(methylsulfanyl)pyridine
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH3:9])=[N:6][CH:7]=1.[CH3:10][S-:11].[Na+]>CN(C=O)C.C(OCC)C>[CH2:8]([C:5]1[CH:4]=[CH:3][C:2]([S:11][CH3:10])=[CH:7][N:6]=1)[CH3:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A solution of 5-bromo-2-ethylpyridine (see part (i)) (3.0 g, 16.2 mmol) in dry DMF (4.5 ml) was treated with sodium methanethiolate (1.8 g, 24.3 mmol) and the suspension heated at 100° C. for 3 hours. The cooled mixture was diluted with diethyl ether (200 ml), washed with water (4×100 ml), then dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica by elution with dichloromethane. The appropriate fractions were combined and evaporated under reduced pressure. The resulting oil was distilled under reduced pressure (60 mm) at an oven temperature of 150° C. using a Kugelrohr (trade mark) apparatus to give the title compound, (1.4 g).
Workup
- washwashed with water (4×100 ml)
- dry with materialdried (MgSO4)
- customevaporated under reduced pressure
- customThe residue was purified by flash chromatography on silica by elution with dichloromethane
- customevaporated under reduced pressure
- distillationThe resulting oil was distilled under reduced pressure (60 mm) at an oven temperature of 150° C.
Sources & evidence
- ORD record
- ord-dd85cb8ee3bb4e7d86ef1f057b1b127e
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05541203
Reaction notes
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