Diethylamine → HCID 11286670, compound

Temperature

0 °C

Pyrrole-2-carboxylic acid (10.0 g, 90 mmol) was dissolved. in 250 mL of dichloromethane. DCC (N,N-dicyclohexylcarbodiimide) (20.4 g, 99 mmol), DMAP (4-dimethyl-aminopyridine) (2.2 g, 18 mmol) and diethylamine (10.2 mL, 99 mmol) were added subsequently at 0° C. under an Argon atmosphere. The reaction mixture was stirred at 0° C. for 30 mins then stirred at root temperature for 8 hours. The solution was diluted with dichloromethane and the solid was filtered off. The filtrates were washed by diluted hydrochloric acid, followed by saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/2) to obtain N,N-diethyl-1H-pyrrole-2-carboxamide as a white solid (10.5 g, 70% yield). mp 78.6-79.9° C.; 1H NMR (300 MHz, CDCl3): δ 10.1 (br, 1H), 6.94-6.88 (m, 1H), 6.57-6.51 (m, 1H), 6.26-6.21 (m, 1H), 3.95-3.86 (m, 4H), 1.31-1.24 (m, 6H); 13C NMR (75.5 Hz, CDCl3): δ 161.9, 120.7, 111.3, 110.1, 109.5, 41.9, 13.4; IR (CH2Cl2) 3442, 2981, 2937, 1716, 1600 cm−1; LRMS (EI) m/z (%) 166 (M+; 100); HRMS (EI): calcd for C9H14N2O: 166.1106, Found: 116.1106.

1. stirringthen stirred at root temperature for 8 hours
2. filtrationthe solid was filtered off
3. washThe filtrates were washed by diluted hydrochloric acid
4. dry with materialThe organic layer was dried over sodium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/2)

ORD record

ord-24fa9f1f2e4e453e9eb18f9bdd6a67b2

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07705040B2