Pyridine → 5-chloro-N,N-diethyl-2-iodobenzamide

In a 100 mL round bottomed flask was placed the 5-chloro-2-iodobenzoyl chloride prepared above. Pyridine (50 mL, 600 mmol) and tetrahydrofuran (10 mL, 100 mmol) were then added. To the reaction mixture was added diethylamine (3 mL, 30 mmol) and the mixture was stirred for 3 hr at rt. The mixture was stirred for an additional 3 hr at 50° C. The mixture was allowed to cool to rt and then concentrated under reduced pressure. The residue was dissolved in EtOAc (100 mL) and then washed with 1N HCl (50 mL×2), 1N NaOH (50 mL), brine (50 mL), and dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain the title compound (1.96 g, 61%) as a light yellow syrup. LCMS: (FA) ES+ 338, 340; 1H NMR (300 MHz, d6-DMSO) δ ppm 7.86 (d, 1H), 7.38 (d, 1H), 7.21 (dd, 1H), 3.61-3.68 (m, 1H), 2.91-3.29 (m, 3H), 1.17 (t, 3H), 1.01 (t, 3H).

1. customIn a 100 mL round bottomed flask was placed
2. stirringThe mixture was stirred for an additional 3 hr at 50° C
3. temperatureto cool to rt
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was dissolved in EtOAc (100 mL)
6. washwashed with 1N HCl (50 mL×2), 1N NaOH (50 mL), brine (50 mL)
7. dry with materialdried over anhydrous MgSO4
8. customInsoluble materials were removed by filtration
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-7b93011e94204a8487cc9a4c4717080b

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765746B2