Methyl iodide → HCID 22027357, compound

N-(diphenylmethylene)glycine ethyl ester (2.25 g) was added to a suspension of sodium hydride (0.74 g of 60% oil dispersion) in 20 mL of dry N,N-dimethylformamide at room temperature, resulting in vigorous gas evolution. After stirring at room temperature for five minutes, 2 g of 2,3-dichloro-5-trifluoromethylpyridine was added, followed by stirring at room temperature for 1 hour. Then 0.80 mL of methyl iodide was added followed by stirring at room temperature overnight. The reaction mixture was poured onto ice water, extracted with diethyl ether (2×), and distilled under vacuum to remove the solvent leaving an oil. The oil was then refluxed in 6 N HCl overnight. The reaction mixture was cooled to room temperature, made basic with solid sodium carbonate and extracted with diethyl ether (2×). The combined extracts were dried over magnesium sulfate and distilled under vacuum to remove the solvent, leaving 1.5 g of an oil. 1H NMR (CDCl3; 300 MHz) δ 1.4 (d, 3H, J is 6.6 Hz), 4.6 (bs, 1H), 7.88 (m, 1H), 8.75 (bs, 1H).

1. customresulting in vigorous gas evolution
2. stirringby stirring at room temperature for 1 hour
3. stirringby stirring at room temperature overnight
4. additionThe reaction mixture was poured onto ice water
5. extractionextracted with diethyl ether (2×)
6. distillationdistilled under vacuum
7. customto remove the solvent
8. customleaving an oil
9. temperatureThe reaction mixture was cooled to room temperature
10. extractionextracted with diethyl ether (2×)
11. dry with materialThe combined extracts were dried over magnesium sulfate
12. distillationdistilled under vacuum
13. customto remove the solvent

ORD record

ord-a3080e5880ff42ab9444ce4821a81d0d

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07074742B2