Carbon Disulfide → HCID 58035957, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−10° C.) solution of 2-(methylamino)pyridine (1.71 g; 15.8 mmol) in dry THF (50 mL) was added n-butyl lithium (1.6M in hexane) (10 mL, 16 mmol) over 30 minutes under an inert atmosphere. The resultant pale yellow mixture was allowed to stir at −10° C. for one hour and then warmed to 0° C. before the dropwise addition of carbon disulfide (1.58 g, 20.8 mmol); the resultant solution was allowed to stir at room temperature for one hour. Methyl 2-bromopropionate (2.84 g, 17 mmol) was added dropwise and allowed to stir for 2 hours. THF was removed in vacuo, the mixture was suspended in ethyl acetate and filtered. After in vacuo elimination of the ethyl acetate the crude product was purified by column chromatography using 20% ethyl acetate in n-hexane as eluent to afford the title product (6), an off-white solid (2.32 g, 54.3% yield). 1H nmr (CDCl3) δ (ppm) 1.50 (d, 3H, CHCH3); 3.70 (s, 3H, COOCH3 or N—CH3); 3.75 (s, 3H, COOCH3 or N—CH3); 4.70 (q, 1H, CHCH3); 7.30-7.40 (m, 2H, ArH); 7.80 (m, 1H, ArH); 8.60 (m, 1H, ArH).

Provenance & Evidence