Dimethylformamide → HCID 89543448, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round bottom flask was added methyl 5-bromopyridine-2-carboxylate (5 g, 23.14 mmol), DMF (50 mL) and sodium propane-2-thiolate (5.678 g, 57.85 mmol). The reaction was placed in a pre-heated 65° C. oil bath and was stirred for 3 h. The reaction was allowed to cool to 25° C. and the reaction was quenched with brine. The reaction was extracted with ethyl acetate. The two layers were separated in a reparatory funnel. The aqueous layer was kept and collected in a 1 L Erlenmeyer flask. The organic layer was discarded. The aqueous layer was then treated with 24 mL of Clorox bleach drop-wise over 1 h and allowed to stir overnight. By LCMS, the reaction showed a small amount of sulfone, and about a 50:50 mixture of sulfoxide and thio ether. The reaction was then acidified to pH 2 with HCl. The reaction mixture was then extracted with ethyl acetate 3 times, separated, and the organic layers were collected. The organic layers were then washed with brine 3 times to remove DMF. The aqueous layer was then evaporated to dryness to give 5-(isopropylsulfinyl)picolinic acid (2.10 g) as a white solid; ESI-MS m/z talc. 213.0, found 214.2 (M+1)+; Retention time: 0.87 minutes (3 min run).

Provenance & Evidence