Sodium Sulfide → HCID 131721058, compound

Participants

Reaction Steps

To nitrosonium tetrafluoroborate (NOBF4) (22 mg, 0.19 mmol) in methylene chloride (6 ml) at room temperature is added [(5-amino-2-pyridinyl)aminomethylene]bis[phosphonic acid] tetraethyl ester (75 mg, 0.19 mmol). The reaction mixture is stirred 3 hours then concentrated under reduced pressure. The crude residue is dissolved in acetonitrile (6 ml) and sodium sulfide (46 mg, 0.19 mmol) is added. After stirring 12 hours at room temperature, the reaction is quenched by the addition of water and the mixture is extracted with methylene chloride. The organic extracts are combined and washed with 10% aqueous Na2S2O3. The organic extracts are then dried over sodium sulfate, filtered and concentrated under reduced pressure. The desired thiol is obtained by flash chromatography purification with 2% isopropanol in methylene chloride.

Provenance & Evidence