Sodium methanethiolate → 5-Acetyl-3-chloro-2-methylthiopyridine

HRID 2304541Notes

Reaction equation

HRID 2304541 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Cl:11])[C:7](Cl)=[N:8][CH:9]=1)(=[O:3])[CH3:2].[CH3:12][S-:13].[Na+]>C(O)(C)(C)C.O.CCOCC>[C:1]([C:4]1[CH:5]=[C:6]([Cl:11])[C:7]([S:13][CH3:12])=[N:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 4378561Sodium methanethiolateHCID 101980061-(5,6-Dichloropyridin-3-yl)ethan-1-one

Product 1

HCID 184358025-Acetyl-3-chloro-2-methylthiopyridineYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent

Procedure

5-Acetyl-2,3-dichloropyridine (24.5 g, 0.129 mol) was slurried in t-butanol (200 mL) and sodium methanethiolate (10 g, 0.143 mol) was added. The mixture was heated under reflux conditions for two hours, cooled to room temperature, and diluted with water (200 mL) and ether (150 mL). This was separated and the aqueous phase extracted with ether (50 mL). The combined organic extracts were washed with water (100 mL) and saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulphate, and evaporated to dryness to give the desired product (24.1 g, 94%) as a pale, low melting solid.

Workup

  1. temperatureThe mixture was heated under reflux conditions for two hours
  2. customThis was separated
  3. extractionthe aqueous phase extracted with ether (50 mL)
  4. washThe combined organic extracts were washed with water (100 mL) and saturated sodium chloride solution (100 mL)
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-23c56eaf6b234f50b4d908973966e4aa
Source dataset
uspto-grants-2002_08
Patent number
US06436963B1

Reaction notes

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