Thionyl Chloride → 5-(chloromethyl)-1-methyl-1H-imidazole hydrochloride

Temperature

-5 °C

A mixture of (1-methyl-1H-imidazol-5-yl)methanol (500 mg, 4.5 mmol) in DMF (5 mL) at −5° C. was slowly treated with thionyl chloride (0.49 mL, 6.7 mmol), stirred an additional 10 minutes at −5° C., warmed to room temperature, stirred 1.5 hours, cooled to −5° C., quenched with isopropyl alcohol and ethyl acetate, stirred 30 minutes at −5° C., concentrated under vacuum, and filtered to collect the solid. The solid was rinsed with ethyl acetate and dried under vacuum to give (212 mg, 28%) of the desired product as the hydrochloride salt. MS (DCI) m/e 131 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 9.10 (s, 1H), 7.76 (s, 1H), 5.02 (s, 2H), 3.88 (s, 3H).

1. temperaturewarmed to room temperature
2. stirringstirred 1.5 hours
3. temperaturecooled to −5° C.
4. customquenched with isopropyl alcohol and ethyl acetate
5. stirringstirred 30 minutes at −5° C.
6. concentrationconcentrated under vacuum
7. filtrationfiltered
8. customto collect the solid
9. washThe solid was rinsed with ethyl acetate
10. customdried under vacuum

ORD record

ord-1d06ad99f73240f2845b8af79e53e235

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456169B2