Methanesulfonic Acid → (5-Chloro-2-ethyl-1h-imidazol-4-yl)methanol

A solution of 4-chloro-2-ethyl-5-{[(phenylmethyl)oxy]methyl}-1H-imidazole (2.51 g, 10.0 mmol) and methanesulfonic acid (25 mL, 385 mmol) in chloroform (56 mL) was stirred at RT for 1 h. The reaction mixture was poured into ice (˜100 g) and the solution was neutralized by addition of 5N NaOH until the pH was 10. The solution was extracted with methyl tert-butyl ether (2×100 mL) and then with n-butanol (3×100 mL). The combined n-butanol extracts were concentrated, azeotroped with toluene, and dried in vacuo to provide the title compound in quantitative yield as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.10 (br. s., 1H), 5.10 (br. s., 1H), 4.32 (s, 2H), 2.54 (q, 2H), 1.15 (t, 3H).

1. extractionThe solution was extracted with methyl tert-butyl ether (2×100 mL)
2. concentrationThe combined n-butanol extracts were concentrated
3. customazeotroped with toluene
4. customdried in vacuo

ORD record

ord-b10790d9ca0f42f48f79761e233ee1dd

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304419B2