Iodine → HCID 178432963, compound

Into a 25-mL round bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of 4-methyl-1H-imidazole-2-carbonitrile (compound 14.2, 350 mg, 3.27 mmol) and aqueous sodium hydroxide (2 M, 5 mL) and stirred for 15 min at room temperature. This was followed by the drop-wise addition of a solution of iodine (1.25 g, 4.92 mmol) in dichloromethane (5 mL). The resulting mixture was stirred for 24 h at room temperature, then diluted with water/ice (10 mL). The aqueous layer was washed with DCM (10 mL), and then the aqueous layer was acidified to pH 5-6 with acetic acid. The aqueous phase was extracted with EtOAc (5×50 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to yield 500 mg (66%) of the title compound as a brown solid.

1. customInto a 25-mL round bottom flask, which was purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe resulting mixture was stirred for 24 h at room temperature
4. washThe aqueous layer was washed with DCM (10 mL)
5. extractionThe aqueous phase was extracted with EtOAc (5×50 mL)
6. dry with materialthe combined organic layers were dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-db6de2e960fd4d40b31e5486db54848a

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2