Chloromalonaldehyde → HCID 46785475, compound

To a solution of 3-(trifluoromethyl)benzenecarbothioamide (1.31 g, 6.37 mmol) in ethanol (15 mL) was added 2-chloropropane-1,3-dial (2.04 g, 19.1 mmol), and the mixture was heated under reflux overnight. The reaction mixture was extracted with ethyl acetate, washed successively with diluted aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give 2-[3-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde (423 mg) as colorless crystals. The present compound was dissolved in ethanol (5 mL), sodium borohydride (91 mg, 2.47 mmol) was added under ice-cooling, and the mixture was stirred at room temperature overnight. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (334 mg, 78%) as a colorless oil.

1. temperaturethe mixture was heated
2. temperatureunder reflux overnight
3. extractionThe reaction mixture was extracted with ethyl acetate
4. washwashed successively with diluted aqueous sodium hydrogen carbonate solution and saturated brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

ORD record

ord-26f4d5995d3445e0aa39835722c95cb5

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461348B2