1,3-Dibromo-5,5-dimethylhydantoin → HCID 14181260, compound

Participants

Reaction Steps

1,3-Dibromo-5,5-dimethylhydantoin (3.45 g, 12 mmol), sodium bicarbonate (400 mg) and lauroyl peroxide (50 mg) were added to a solution of (22E)-5,22-ergostadiene-1α,3β-diol diacetate (IX) (10.0 g, 20 mmol) in hexane (150 ml). The reaction solution was stirred under reflux for 25 minutes. After cooling, the crystals were separated by filtration from the reaction mixture and hexane was distilled off from a filtrate. The residue was dissolved in butyl acetate (80 ml) and added dropwise to a solution of quinaldine (14.3 g, 100 mmol) in butyl acetate (70 ml) with stirring under reflux. The mixture was further refluxed for 40 minutes. After cooling, the reaction mixture was washed successively with 2N hydrochloric acid, water, saturated sodium bicarbonate solution and saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to give a crude (22E)-5,7,22-ergostatriene-1α,3β-diol diacetate (III) which was dissolved in chloroform (50 ml) and a solution of 4-phenyl-1,2,4-triazoline-3,5-dione (2.26 g, 13 mmol) in acetone (40 ml) was added dropwise with stirring at room temperature. After concentration of the reaction mixture, the resulting residue was purified by silica gel column chromatography eluting with 2/1 hexane/ethyl acetate to give 3.5 g of the foamy title compound (IV).

Provenance & Evidence