4-Methoxybenzenethiol → HCID 22181674, compound

Participants

Reaction Conditions

Reaction Steps

4-Methoxythiophenol (1.7 mL, 13.85 mmol) was added to a suspension of NaH 60% in oil (831 mg, 20.80 mmol) in DMF (30 mL) at 0° C., and the mixture was allowed to warm to 25° C. 3-Iodo-6-methyl-1H-pyridin-2-one (3 g, 12.78 mmol) was added to the solution at 0° C., followed by CuI (533 mg, 2.8 mmol). The reaction was stirred at 25° C. for 1 h and heated at 120° C. for 5 h. It was then allowed to cool and partitioned between CH2Cl2 (30 mL) and 9:1 NH4Cl/NH4OH (30 mL) and stirred for 15 min. The mixture was extracted with CH2Cl2 (3×70 mL each) and the combined CH2Cl2 extracts were washed with water (3×30 mL), brine, dried and stripped in vacuo to give the crude product (3.6 g), which was further purified by washing with ether to give 2.93 g of 3-(4-methoxyphenylsulfanyl)-6-methyl-1H-pyridin-2-one which was used in the next step.

Provenance & Evidence