Isopropanol → 3-bromo-N-(4-methoxybenzyl)-1,2,4-thiadiazol-5-amine

A round-bottom flask was charged with 3-bromo-5-chloro-1,2,4-thiadiazole (2.73 g, 13.69 mmol), i-PrOH (25 mL), and triethylamine (3.82 ml, 27.4 mmol) to give a clear solution. 4-Methoxybenzylamine (2.132 ml, 16.42 mmol) was added dropwise at room temperature, and the resulting mixture was stirred for 2 h before being diluted with EtOAc. The organic solution was washed with saturated aq. sodium bicarbonate solution, washed with water, washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude product was purified by chromatography on silica gel (0 to 40% EtoAc/Heptane) to give a white solid. The solid was suspended in heptane, and the slurry was filtered. The collected solid was washed with heptane (3×), then dried under a stream of N2 overnight to give 3-bromo-N-(4-methoxybenzyl)-1,2,4-thiadiazol-5-amine (2.774 g, 9.24 mmol, 67.5% yield) as a white, fluffy solid. 1H NMR (400 MHz, DMSO-d6) δ=9.20 (br. s., 1 H), 7.33-7.20 (m, 2 H), 7.01-6.84 (m, 2 H), 4.43 (br. s., 2 H), 3.74 (s, 3 H). m/z (ESI) 300.0 (M+H)+.

1. customto give a clear solution
2. washThe organic solution was washed with saturated aq. sodium bicarbonate solution
3. washwashed with water
4. washwashed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by chromatography on silica gel (0 to 40% EtoAc/Heptane)
9. customto give a white solid
10. filtrationthe slurry was filtered
11. washThe collected solid was washed with heptane (3×)
12. dry with materialdried under a stream of N2 overnight

ORD record

ord-f803ef8f142549049e48f0255ef9607e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079902B2