1,3-Dibromo-5,5-dimethylhydantoin → 7-Bromo-3 beta,25-dibenzoyloxycholest-5-ene

HRID 1834203Notes

Reaction equation

HRID 1834203 reaction equation
[C:1]([O:9][C@H:10]1[CH2:43][CH2:42][C@@:41]2([CH3:44])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:40]2[CH2:39][CH2:38][C@@:37]2([CH3:45])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:36])[CH2:21][CH2:22][CH2:23][C:24]([O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH3:26])[CH3:25])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:46]N1C(=O)C(C)(C)N(Br)C1=O>CCCCCC>[Br:46][CH:14]1[CH:13]=[C:12]2[C@:41]([CH3:44])([CH2:42][CH2:43][C@H:10]([O:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:11]2)[C@@H:40]2[C@@H:15]1[C@H:16]1[C@:37]([CH3:45])([CH2:38][CH2:39]2)[C@@H:19]([C@H:20]([CH3:36])[CH2:21][CH2:22][CH2:23][C:24]([O:27][C:28](=[O:35])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([CH3:26])[CH3:25])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 155418583beta,25-Dibenzoyloxycholest-5-ene

Product 1

HCID 228012527-Bromo-3 beta,25-dibenzoyloxycholest-5-ene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a boiling solution of 2.02 gm. of 3β,25-dibenzoyloxycholest- 5-ene (3.3 mmole) in 90 ml. of hexane, and 720 mg. (2.52 mmole) of dibromo-dimethylhydantoin. Reflux for 30 minutes, cool to room temperature, filter and wash with 2 ml. of carbontetrachloride. Concentrate the combined filtrate to dryness to obtain the title product. (2.3 gm.)

Workup

  1. temperatureReflux for 30 minutes
  2. filtrationfilter
  3. washwash with 2 ml
  4. concentrationConcentrate the combined filtrate to dryness

Sources & evidence

ORD record
ord-ff14b111691848efa48514ca086cf2b8
Source dataset
uspto-grants-1978_01
Patent number
US04069321

Reaction notes

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