Sodium methanethiolate → HCID 86634499, compound

Air in a 20 ml Schlenk tube was replaced by Ar gas and 1.02 g (7 mmol) of m-ethynylbenzoic acid and 5 g (42 mmol) of thionyl chloride were added to the tube and the mixture was stirred at 50° C. for 2 hours and then excess thionyl chloride was removed by distillation under reduced pressure to obtain m-ethynylbenzoyl chloride. To the m-ethynylbenzoyl chloride obtained was added 7 ml of dichloromethane and the resultant mixture was ice-cooled. Then, 515 mg (7.35 mmol) of sodium methanethiolate was added to the mixture and the mixture was stirred at room temperature for 3 hours. After completion of the stirring, dichloromethane was removed by distillation under reduced pressure and 35 ml of water was added to the resultant residue. The mixture was extracted with 35 ml of ethyl acetate and the extract was dried over magnesium sulfate and the solvent was removed by distillation under reduced pressure using an evaporator. The resultant crude reaction product was purified by column chromatography (Hexane/AcOEt=10/1) using silica gel to obtain 0.49 g of S-methyl 3-ethynyl-thiobenzoate which is a desired product as yellow solid. (Yield: 40%)

1. temperaturecooled
2. customAfter completion of the stirring, dichloromethane was removed by distillation under reduced pressure and 35 ml of water
3. additionwas added to the resultant residue
4. extractionThe mixture was extracted with 35 ml of ethyl acetate
5. dry with materialthe extract was dried over magnesium sulfate
6. customthe solvent was removed by distillation under reduced pressure
7. customan evaporator
8. customThe resultant crude reaction product
9. customwas purified by column chromatography (Hexane/AcOEt=10/1)

ORD record

ord-732e56ad36504b6b854895f79c514c6b

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932398B2