Ammonium Chloride → HCID 178432683, compound

To a solution of 4-iodo-1-tritylimidazole (6.88 g, 15.8 mmol) in 65 mL anhydrous dichloromethane was added 6.3 mL of a solution of ethyl magnesium bromide (3.0 M, 18.9 mmol) in diethyl ether under argon. The reaction mixture was stirred for 2.5 h, and then a solution of N-methoxy, N-methyl-2-methylnicotinamide (2.84 g, 15.8 mmol) was added. After 5 days of stirring, the reaction mixture was poured into saturated aqueous ammonium chloride solution (125 mL). The layers were separated, and the aqueous layer was extracted twice with dichloromethane (50 mL). The organic extracts were combined, dried (Na2SO4), and concentrated to provide a red-orange foam which was purified on flash silica gel (1% methanol-chloroform to 2% methanol-chloroform) to provide the desired product as 5.56 g (82%) of a golden-brown foam. MS (PB-NH3), m/z 430 (MH+). 1H NMR (CDCl3) δ 2.63 (s, 3H), 7.02-7.16 (m, 7H), 7.19 (dd, J=7.8, 5.1 Hz, 1H), 7.28-7.41 (m, 8H), 7.49 (d, J=0.9 Hz, 1H), 7.70 (d, J=0.9 Hz, 1H), 7.96 (dd, J=7.9, 1.2 Hz, 1H), 8.57 (dd, J=7.9, 4.9 Hz, 1H.

1. stirringAfter 5 days of stirring
2. customThe layers were separated
3. extractionthe aqueous layer was extracted twice with dichloromethane (50 mL)
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated
6. customto provide a red-orange foam which
7. customwas purified on flash silica gel (1% methanol-chloroform to 2% methanol-chloroform)

ORD record

ord-731ae8ac3bcb48a9b540a308ec397f93

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06465486B1