Benzoyl chloride → HCID 22225917, compound

Participants

Reaction Steps

General Method A. A solution of 1.71 M tin (IV) chloride (3.1 mL, 5.3 mmole) in 1,2-dichloroethane was added dropwise to a suspension of 9 (0.241 g, 1.42 mmole) and benzoyl chloride (0.31 mL, 2.66 mmole) in 1,2-dichloroethane and the mixture was refluxed for 10.5 hours. The reaction was quenched with ice and the organic phase was washed sequentially with 2N HCI, water and 2N NaOH. Drying over CaCl2 and evaporation gave a solid that was purified by chromatography on silica gel eluted with pet. ether-ethyl acetate 5:1. Recrystallization from water:gave 0.32 g of pure product as yellow crystals, 82%. 1H NMR (CDCl3) δ: 1.6 (s, 3H, CH3), 2.23.(s, 3H, CH3), 2.24 (s, 3H, CH3), 7.4–7.6 (m, 5H, C6H5), 11.1 (br s, 1H, NH.) 13C NMR (CDCl3) δ: 12.4, 14.8, 23.6, 122.4, 124.7, 127.6, 128.3, 128.4, 131.9, 140.3, 146.4, 167.4, 195.0.

Provenance & Evidence