Hydrochloric Acid → HCID 10943963, compound

Temperature

160 °C

1-(4-bromo-2-thienyl)-2-methyl-1-propanone (816 mg, 3.52 mmol) was diluted in ethylene glycol (3 mL). Hydrazine monohydrate (0.46 mL, 9.5 mmol, 2.7 eq) was added, and the mixture was heated to 160° C. for 1.5 h behind a blast shield. The mixture was cooled to rt, and diluted with water. 6 M aqueous HCl was added until pH was acidic (pH paper), and the mixture was extracted three times with hexanes. The combined organics were dried over sodium sulfate, filtered, and concentrated. The crude product was purified by biotage, 25M+ column, eluting with 5% ethyl acetate in hexanes. Fractions containing the desired product were concentrated in vacuo to afford the title compound as light yellow oil (192 mg, 25%).

1. temperatureThe mixture was cooled to rt
2. extractionthe mixture was extracted three times with hexanes
3. dry with materialThe combined organics were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude product was purified by biotage, 25M+ column
7. washeluting with 5% ethyl acetate in hexanes
8. additionFractions containing the desired product
9. concentrationwere concentrated in vacuo

ORD record

ord-5ede45b01faf4fe998678ddf8938c08d

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071584B2