Hydrochloric Acid → HCID 178482490, compound

Participants

Reaction Conditions

Reaction Steps

4,5-Dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl formamide (39.6 g, 129.2 mmole) was dissolved in dry tetrahydrofuran (500 ml) with warming and then cooled to 10° C. with stirring. Borane dimethylsulfide complex (10M, 80 ml, 800 mmole) was added dropwise by syringe through a septum cap. The reaction mixture was heated on a steam bath for ca 12 hrs (overnight), cooled in an ice bath, methanol (150 ml) added dropwise and the mixture stirred for 1 hr until the effervescence had subsided. Concentrated hydrochloric acid (30 ml) was then added to give a clear solution. This was poured into water (51) and extracted with ethyl acetate (×2) and the extract washed and dried (MgSO4). Evaporation of the solvent left a white glass which was dried under vacuum for 2 hrs. The yield of product was 33.4 g, 88%.

Provenance & Evidence