Chloroacetone → HCID 11053210, compound

A mixture of sulfur (90 mg, 2.96 mmol), sodium hydrosulfide hydrate (250 mg, 4.44 mmol) and sodium carbonate (330 mg, 2.37 mmol) in N-methylpyrrolidine (10 mL) was stirred at rt for 1 h. A solution of 2-fluoro-5-nitrobenzaldehyde (500 mg, 2.96 mmol) in N-methylpyrrolidine (2 mL) was added dropwise and the mixture was stirred at rt for 3 h. Chloroacetone (270 mg, 2.96 mmol) was added slowly with cooling and the resulting mixture was stirred at rt overnight. The reaction was quenched with 20 mL of water and sodium hydroxide (1 M) was added to adjust pH to 11. The mixture was extracted with diethyl ether (3×50 mL) and the combined organic layer was washed with brine (100 mL), dried over sodium sulfate and filtered. After removing the solvent in vacuo the product was recrystallized from methanol to give a yellow solid (400 mg, 62%). MS (M+H)+ 222.

1. stirringthe mixture was stirred at rt for 3 h
2. temperaturewith cooling
3. stirringthe resulting mixture was stirred at rt overnight
4. customThe reaction was quenched with 20 mL of water and sodium hydroxide (1 M)
5. additionwas added
6. extractionThe mixture was extracted with diethyl ether (3×50 mL)
7. washthe combined organic layer was washed with brine (100 mL)
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. customAfter removing the solvent in vacuo the product
11. customwas recrystallized from methanol

ORD record

ord-cb742f49d87548dcaa22140d71524146

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786132B2