Methanesulfonic Acid → (4-chloro-2-propyl-1H-imidazol-5-yl)methanol

A solution of 4-chloro-5-{[(phenylmethyl)oxy]methyl}-2-propyl-1H-imidazole (1.72 g, 6.5 mmol) and methanesulfonic acid (16 mL, 247 mmol) in chloroform (36 mL) was stirred at RT for 1 h. The reaction mixture was poured into ice (˜70 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 (2×60 mL) and then with n-butanol (3×40 mL). The combined n-butanol extracts were concentrated, washed with brine, and dried in vacuo to provide the title compound (0.927 g, 82%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.09 (br. s., 1H), 5.10 (br. s., 1H), 4.31 (s, 2H), 2.45-2.51 (m, 2H), 1.60 (sex, 2H), 0.87 (t, 3H).

1. extractionThe solution was extracted with methyl tert-butyl ether (2×60 mL)
2. concentrationThe combined n-butanol extracts were concentrated
3. washwashed with brine
4. customdried in vacuo

ORD record

ord-4fe9f3c5e8a54e7d8f1da7be70a7fa81

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304419B2