Ethanol → Propanoic acid, 3-ethoxy-3-imino-, ethyl ester

Ethyl cyanoacetate (8 mL, 75 mmol) in anhydrous benzene (100 mL) was combined under nitrogen with anhydrous ethanol (6 mL, 105 mmol). The mixture was cooled to 10° C. (ice/acetone) and bubbled 20 minutes with dry hydrogen chloride gas. The mixture was slowly warmed to room temperature, sealed and stirred for approximately 18 hours. The mixture was diluted with diethyl ether (400 mL) and let stand for 5 hours at room temperature to give a crystalline solid. The solid was isolated by filtration, washed several times with anhydrous diethyl ether and dried to provide ethyl 3-ethoxy-3-iminopropionate (13.2 g, 90% yield) as a colorless, crystalline solid; 1H-NMR (300 Mhz, CDCL3): 7.84 (d, 1H, J=10.0 Hz), 7.19-7.36 (m, 5H), 7.00-7.06 (m, 2H), 4.10 (t, 2H, J=5.7 Hz), 2.73 (t, 2H, J=6.5 Hz), 1.89 (m, 4H).

1. custombubbled 20 minutes with dry hydrogen chloride gas
2. customsealed
3. additionThe mixture was diluted with diethyl ether (400 mL)
4. waitlet stand for 5 hours at room temperature
5. customto give a crystalline solid
6. customThe solid was isolated by filtration
7. washwashed several times with anhydrous diethyl ether
8. customdried

ORD record

ord-ac8807b3f6ea4531ac445c635a0b4252

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562854B2