Methyl fluorosulfate → HCID 12370270, compound

Participants

Reaction Steps

A solution of 18.7 g. (0.091 mole) of dried 1-(4-chlorophenyl)-4(1H)-pyridinone [prepared by the process set forth in D. Vorlander, Ber., 58, 1908 (1925)] in 160 ml. of dimethoxyethane was heated to reflux. Without further external heating, 14.2 g. (0.123 mole) of methyl fluorosulfonate was added gradually. The mixture boiled vigorously during the addition and crystalline product started to separate. After the addition was complete, the mixture was stirred at room temperature for 1 hour and then cooled to 10° C. The product was collected by filtration, washed with cold dimethoxyethane and ether and dried in vacuo: yield 28.0 g. (96.5%); m.p. 182°-185° C.; NMR (DMSO-d6) δ4.26 (s, 3H, CH3O), 6.27 (d, 2H, β-pyridyl H), 6.32 (s, 4H, aromatics), 7.62 (d, 2H, α-pyridyl H). The elemental analyses for C, H, N and Cl were within ±0.4 % of the theoretical values.

Provenance & Evidence