1,3-Dibromo-5,5-dimethylhydantoin → HCID 22823419, compound

Participants

Reaction Steps

A solution of 1α,3β-diethoxycarbonyloxycholest-5-ene (5.46 g, 10 m moles), dry hexane (100 ml) and 1,3-dibromo-5,5-dimethylhydantoin (1.716 g, 6 m moles) was reacted at the oil bath temperature of 95° C. under the irradiaton of infrared rays for 15 minutes. The reaction mixture was cooled, and the resulting 5,5-dimethylhydantoin and the excessive 1,3-dibromo-5,5-dimethylhydantoin were removed by filtration. The filtrate was concentrated at reduced pressure to afford a residual product. Xylene was added to this substance to form a solution. The resulting solution was added dropwise to a solution held at 170° C. of s-collidine (25 ml) in dry xylene (33 ml), and the reaction was carried out for additional 20 minutes. After the reaction, the hydrobromide of s-collidine was removed by filtration and the filtrate was concentrated under reduced pressure to give residual product. The residue was dissolved in ethyl acetate (200 ml). The ethyl acetate solution was washed with 1 N hydrochloric acid (3×100 ml), saturated sodium bicarbonate and water, and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to give 6.68 g of residual product.

Provenance & Evidence