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

HRID 1534196Notes

Reaction equation

HRID 1534196 reaction equation
BrN1C(C)(C)C(=O)N(Br)C1=O.C(=O)(O)[O-].[Na+].C(OOC(=O)CCCCCCCCCCC)(=O)CCCCCCCCCCC.[C:45]([O:48][C@@H:49]1[C@@:74]2([CH3:75])[C:53](=[CH:54][CH2:55][C@@H:56]3[C@@H:73]2[CH2:72][CH2:71][C@@:70]2([CH3:76])[C@H:57]3[CH2:58][CH2:59][C@@H:60]2[C@H:61]([CH3:69])/[CH:62]=[CH:63]/[C@H:64]([CH3:68])[CH:65]([CH3:67])[CH3:66])[CH2:52][C@@H:51]([O:77][C:78](=[O:80])[CH3:79])[CH2:50]1)(=[O:47])[CH3:46].N1C2C(=CC=CC=2)C=CC=1C>CCCCCC.C(OCCCC)(=O)C>[C:45]([O:48][C@@H:49]1[C@@:74]2([CH3:75])[C:53](=[CH:54][CH:55]=[C:56]3[C@@H:73]2[CH2:72][CH2:71][C@@:70]2([CH3:76])[C@H:57]3[CH2:58][CH2:59][C@@H:60]2[C@H:61]([CH3:69])/[CH:62]=[CH:63]/[C@H:64]([CH3:68])[CH:65]([CH3:66])[CH3:67])[CH2:52][C@@H:51]([O:77][C:78](=[O:80])[CH3:79])[CH2:50]1)(=[O:47])[CH3:46]

Participants

8

Reactant 5

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 70602-MethylquinolineHCID 7773Lauroyl peroxideHCID 516892Sodium BicarbonateHCID 86745463HCID 86745463, compound

Product 1

HCID 14181260HCID 14181260, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 31272Butyl AcetateSolvent

Procedure

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).

Workup

  1. temperatureunder reflux for 25 minutes
  2. temperatureAfter cooling
  3. customthe crystals were separated by filtration from the reaction mixture and hexane
  4. distillationwas distilled off from a filtrate
  5. dissolutionThe residue was dissolved in butyl acetate (80 ml)
  6. stirringwith stirring
  7. temperatureunder reflux
  8. temperatureThe mixture was further refluxed for 40 minutes
  9. temperatureAfter cooling
  10. washthe reaction mixture was washed successively with 2N hydrochloric acid, water, saturated sodium bicarbonate solution and saturated sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationAfter filtration
  13. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6c9a79d57eed478190fb65047da6219a
Source dataset
uspto-grants-1992_02
Patent number
US05087709

Reaction notes

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