Hydrochloric Acid → HCID 18441887, compound

To 120 ml of dichloromethane solution of (2,4-difluorophenyl)acetic acid (10 g, 58.1 mmol) at 0° C., 1,1′-carbonyldiimidazole (9.4 g, 58.1 mmol) was added slowly. The mixture was then stirred for 2.5 hours at room temperature. The solvent was removed. Then the solid residue was triturated with diethyl ether and dried. The white fluffy solid 1-[(2,4-difluorophenyl)acetyl]-1H-imidazole was used for the next step without further purification. In a separate flask, to the 100 ml of dimethyl sulfoxide solution of potassium tert-butoxide (7.2 g, 63.9 mmol) at 0° C., nitromethane (4.6 g, 75.5 mmol) was added. After stirring for 5 minutes, the 1-[(2,4-difluorophenyl)acetyl]-1H-imidazole made previously was added slowly. The mixture was left stirring overnight while the temperature was gradually warmed up to room temperature. The reaction mixture was poured into 250 ml water and then acidified with 2N HCl to pH=4. The aqueous was extracted with ethyl acetate. After washing with brine and drying with sodium sulfate, removal of the solvent afforded 9.4 g yellowish solid. 1H-NMR (400 MHz, CD3OD) δ 7.18 (m, 1H), 6.82 (m, 2H), 5.30 (s, 2H), 3.82 (s, 2H) ppm. ESI-MS m/z 214 (M−H)−.

1. customThe solvent was removed
2. customThen the solid residue was triturated with diethyl ether
3. customdried
4. customThe white fluffy solid 1-[(2,4-difluorophenyl)acetyl]-1H-imidazole was used for the next step without further purification
5. stirringAfter stirring for 5 minutes
6. waitThe mixture was left
7. stirringstirring overnight while the temperature
8. temperaturewas gradually warmed up to room temperature
9. extractionThe aqueous was extracted with ethyl acetate
10. washAfter washing with brine
11. dry with materialdrying with sodium sulfate, removal of the solvent

ORD record

ord-a9545760d1ac4e88bd648638f3384c6b

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07189851B2