Benzoyl chloride → 3-Benzoyl-4,5-dimethylthiophene-2-carboxylic acid methylamide

Participants

Reaction Steps

A solution of 10 (0.40 g, 2.37 mmole) in 20 mL dry THF was cooled to −70° C. and stirred during the addition of t-butyllithium (5.21 mmole). After 30 minutes of stirring benzoyl chloride (0.42 g=0.35 mL, 3 mmole) was added and the mixture was warmed to room temperature. Workup consisted of quenching the reaction with saturated aqueous NH4Cl and extraction of product into ethyl acetate. The extract was dried over MgSO4, evaporated and product purified by chromatography on silica gel eluted with hexane-ethyl acetate 1:1. Yield 0.356 g, 55% 1H NMR(CDCl3) δ: 1.83 (s, 3H, CH3), 2.37 (s, 3H, CH3), 2.79 (d, 3H, NHCH3), 6.58 (br s, 1H, NH), 7.42–7.78 (m, 5H, ArH).

Provenance & Evidence