Thionyl Chloride → HCID 14294197, compound

Participants

Reaction Steps

A mixture of [1-[(3-ethoxy-3-oxopropyl)thio]-3,3-dimethylbutylidene]hydrazinecarboxylic acid, methyl ester, thionyl chloride and dichloromethane was heated at reflux for 40 hours and then quenched with ice water. The orange product was extracted twice into ether. The extracts were combined, washed with 0.1N sodium hydroxide twice, water twice, saturated sodium chloride twice, dried and concentrated in vacuo. The resulting orange liquid was evaporated onto 70 g of silica gel. The gel was dried and poured onto a column of silica gel packed in petroleum ether. The column was eluted with a gradient of 1-10% ethyl acetate in petroleum ether. The desired fractions were purified on silica gel preparative TLC plates eluting with 3% ethyl acetate in petroleum ether, giving 2.9 g of the desired compound as a light yellow oil. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90 MHz: 1.23 (t, 3H, J=7.0 Hz, CH3); 1.49 (s, 9H, t-butyl); 2.84 (t, 2H, J=7.0 Hz, CH2CO); 3.59 (t, 2H, SCH2); 4.14 (q, 2H, OCH2).

Provenance & Evidence