1,3-Dibromo-5,5-dimethylhydantoin → HCID 16092330, compound

HRID 358002Notes

Reaction equation

HRID 358002 reaction equation
[Br:1]N1C(=O)C(C)(C)N(Br)C1=O.[C:12]([O:15][C@H:16]1[CH2:40][CH2:39][C@@:38]2([CH3:41])[C:18](=[CH:19][CH2:20][C@@H:21]3[C@@H:37]2[CH2:36][CH2:35][C@@:34]2([CH3:42])[C@H:22]3[CH2:23][CH2:24][C@@H:25]2[C@H:26]([CH3:33])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:17]1)(=[O:14])[CH3:13]>>[C:12]([O:15][C@H:16]1[CH2:40][CH2:39][C@@:38]2([CH3:41])[C:18](=[CH:19][C@@H:20]([Br:1])[C@@H:21]3[C@@H:37]2[CH2:36][CH2:35][C@@:34]2([CH3:42])[C@H:22]3[CH2:23][CH2:24][C@@H:25]2[C@H:26]([CH3:33])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:31])[CH3:32])[CH2:17]1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 2723897Cholest-5-en-3-ol (3.beta.)-, 3-acetate

Product 1

HCID 16092330HCID 16092330, compoundYield 43.5%

Procedure

16.3 g of dibromodimethylhydantoin were added to a solution of 42.8 g of cholesterol acetate in 300 ml of petroleum ether (40°-60° C.). The reaction mixture was refluxed for 1 hour while stirring thoroughly. After cooling, the solid (dimethylhydantoin) was filtered off; the solvent was distilled off from the filtrate under reduced pressure. In order to remove the last traces of solvent, 100 ml of acetone were added, after which the solution was again evaporated under reduced pressure. The residue was recrystallized from 50 ml of acetone; the α-epimer crystallized out at 0° C. After three recrystallizations from acetone, 12.6 g of pure 7α-bromocholesterol acetate were obtained having a melting-point of 113.9°-115.6° C.; according to the bromine content and the NMR spectrum, the substance was 100% pure.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe solid (dimethylhydantoin) was filtered off
  4. distillationthe solvent was distilled off from the filtrate under reduced pressure
  5. customIn order to remove the last traces of solvent, 100 ml of acetone
  6. additionwere added
  7. customafter which the solution was again evaporated under reduced pressure
  8. customThe residue was recrystallized from 50 ml of acetone
  9. customthe α-epimer crystallized out at 0° C
  10. customAfter three recrystallizations from acetone

Sources & evidence

ORD record
ord-664698dd62a249bb85fe8cc250e0e50c
Source dataset
uspto-grants-1984_08
Patent number
US04464298

Reaction notes

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