Thionyl Chloride → HCID 86675000, compound

Participants

Reaction Steps

A solution of 6-amino-N-(1-hydroxy-2-methylpropan-2-yl)picolinamide (0.35 mmol, 74 mg) in CHCl3 was cooled to 0° C. and SOCl2 (2.8 mmol, 200 μL) was added. The mixture was refluxed overnight. After cooling to room temperature, the reaction was quenched with 1 M NaOH. The aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried with MgSO4. The crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=2:1 as eluent). White solid, 76 mg, 95% yield. 1H NMR (500 MHz, CDCl3): 7.93 (br, 1H), 7.57-7.54 (m, 1H), 7.52-7.51 (m, 1H), 6.62 (d, 1H, J=8.0 Hz), 4.51 (br, 2H), 3.94 (s, 2H), 1.52 (s, 6H). 13C NMR (125 MHz, CDCl3): 163.97, 156.83, 148.37, 138.88, 112.33, 111.63, 53.72, 51.19, 25.08. MS (ESI, MeOH): 228 (100%, (M+1)+).

Provenance & Evidence