Water → N,N-Diethyl-3-formylbenzamide

To a solution of 3-carboxybenzaldehyde (5.0 g, 33.3 mmol) in 50 mL of tetrahydrofuran was added carbonyl diimidazole (5.67 g, 35.0 mmol) under Argon. After 1 h of stirring, diethylamine (4.87 g, 66.7 mmol) was added, and the reaction mixture was stirred for 18 h and then refluxed one hour. After cooling, water (50 mL) was added to the reaction flask, and the contents were concentrated on a rotary evaporator. The resulting mixture was extracted three times with dichloromethane (50 mL). These extracts were combined, washed twice with 1 N aqueous hydrochloric acid solution (50 mL) and twice with water (50 mL), dried (Na2SO4), and concentrated to give a yellow oil. This material was purified on flash silica gel (1% methanol-chloroform to 3% methanol-chloroform) to provide 4.68 g (68% yield) of N,N-diethyl(3-formyl)benzamide as a light green oil. MS (ES), m/z 206 (MH+). 300 MHz 1H NMR (CDCl3) δ1.13 (br s, 3H), 1.27 (br s, 3H), 3.26 (br d, J=5.5 Hz, 2H), 3.58 (br d, J=5.5 Hz, 2H), 7.60 (t, J=7.6 Hz, 1H), 7.65 (t, J=7.8 Hz, 1H), 7.87-7.96 (m, 2H), 10.04 (s, 1H).

1. stirringthe reaction mixture was stirred for 18 h
2. temperaturerefluxed one hour
3. temperatureAfter cooling
4. concentrationthe contents were concentrated on a rotary evaporator
5. extractionThe resulting mixture was extracted three times with dichloromethane (50 mL)
6. washwashed twice with 1 N aqueous hydrochloric acid solution (50 mL) and twice with water (50 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. customto give a yellow oil
10. customThis material was purified on flash silica gel (1% methanol-chloroform to 3% methanol-chloroform)

ORD record

ord-f8e978ca40fa4976868d614e3b7ce41c

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576105B2