Sulfuric Acid → 1-[1-(Propan-2-yl)-1H-imidazol-5-yl]ethan-1-one

Temperature

8 °C

In a 300 mL-volume glass vessel equipped with a stirrer, a thermometer and a dropping funnel, the isopropyl alcohol solution containing 13.9 g (0.162 mol) of N-isopropylformamidine (which was prepared in Reference Example 4), 19.3 g (0.108 mol) of 3-bromo-4-methoxy-3-buten-2-one and 16.4 g (0.162 mol) of triethylamine were placed. The mixture was heated to 8° C. under stirring for 8 hours for carrying out reaction. After the reaction was complete, 80 mL of sulfuric acid (2 mol/L) was added to the reaction mixture, and the mixture was concentrated under reduced pressure. The concentrate was washed with methyl isobutyl ketone, and the aqueous portion was taken out. The aqueous portion was made basic by adding an aqueous 48% sodium hydroxide, while the mixture was kept at a temperature of not higher than 40° C. The aqueous basic portion was subjected to extraction with methyl isobutyl ketone, and the extracted portion was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluant: ethyl acetate) to give 3.28 g (yield: 20%) of 5-acetyl-1-isopropylimidazole as pale yellow liquid.

1. customIn a 300 mL-volume glass vessel equipped with a stirrer
2. customreaction
3. concentrationthe mixture was concentrated under reduced pressure
4. washThe concentrate was washed with methyl isobutyl ketone
5. additionby adding an aqueous 48% sodium hydroxide
6. customhigher than 40° C
7. extractionThe aqueous basic portion was subjected to extraction with methyl isobutyl ketone
8. concentrationthe extracted portion was concentrated under reduced pressure
9. customThe concentrate was purified by silica gel column chromatography (eluant: ethyl acetate)

ORD record

ord-0295232c63d34242a3c75e5465b10927

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858807B2