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

HRID 381232Notes

Reaction equation

HRID 381232 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-22e50e9e43b14f3b9775de1aa16d5e0d
Source dataset
uspto-grants-2001_10
Patent number
US06306839B1

Reaction notes

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