N-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amine → 3-fluoro-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-methoxybenzyl)thiazol-2-amine (1 g, 4.577 mmol) in THF (30 mL) was added LiHMDS (1.58 g, 9.09 mmol, Aldrich) at −78° C. and the reaction mixture was stirred at 25° C. for 15 min. Afterward, 3-fluoro-4-nitrobenzene-1-sulfonyl chloride (2.17 g, 9.09 mmol) dissolved in THF was added to the above mixture at −78° C. and reaction mixture was stirred at 25° C. for 1 h. The reaction mixture was cooled to 0° C. and quenched with ice water (70 mL). The organic compound was extracted with EtOAc, washed with water, dried over sodium sulfate and concentrated to get the crude material which was purified by silica gel column chromatography using a gradient of 0-40% EtOAc in hexanes as the eluent to afford 1.1 g of 3-fluoro-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide as light yellow solid in 57.8% yield. 1H-NMR (400 MHz, DMSO): δ 8.12 (t, J=18.8 Hz, 1H), 8.09-8.07 (m, 1H), 7.84 (d, J=8.8 Hz, 1H), 7.49-7.53 (dd, 2H), 7.22-7.32 (m, 2H), 6.88-6.98 (m, 2H), 5.07 (s, 2H), 3.71 (s, 3H).

Provenance & Evidence