Benzoyl Peroxide → HCID 53743300, compound

HRID 1440975Notes

Reaction equation

HRID 1440975 reaction equation
[NH:1]([C:5]1[C:22](=[O:23])[CH:21]=[CH:20][C@@:19]2([CH3:24])[C:6]=1[CH2:7][CH2:8][C@@H:9]1[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]1[CH2:11][CH2:12][C:13]2=[O:25])[C:2]([CH3:4])=[O:3].[Br:26]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:26][C@H:7]1[C:6]2[C@:19]([CH3:24])([CH:20]=[CH:21][C:22](=[O:23])[C:5]=2[NH:1][C:2]([CH3:4])=[O:3])[C@@H:18]2[C@H:9]([C@H:10]3[C@@:14]([CH2:16][CH2:17]2)([CH3:15])[C:13](=[O:25])[CH2:12][CH2:11]3)[CH2:8]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22859497HCID 22859497, compound

Product 1

HCID 53743300HCID 53743300, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-acetamino-androsta-1,4-diene-3,17-dione (3.404 g, 10 mmol) in CCl4 (250 ml) were added N-bromosuccinimide (2.850 g, 16 mmol) and benzoyl peroxide (0.121 g, 0.5 mmol). The solution was heated under reflux for 1 h and then filtered to remove any insoluble material. The filtrate was washed with 5% NaHCO3 solution and with water and the organic phase evaporated to dryness under reduced pressure. The residue was triturated with a small amount of 95% EtOH to give mixture of crude 6α- and 6α-bromoacetamino-androsta-1,4-diene-3,17-dione in 90% yield (3.780 g), which was used in the following fluorination reaction without further purification.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 1 h
  3. filtrationfiltered
  4. customto remove any insoluble material
  5. washThe filtrate was washed with 5% NaHCO3 solution and with water
  6. customthe organic phase evaporated to dryness under reduced pressure
  7. customThe residue was triturated with a small amount of 95% EtOH
  8. customto give
  9. customwas used in the following fluorination reaction without further purification

Sources & evidence

ORD record
ord-c887a624390a482881349f8722dbff4d
Source dataset
uspto-grants-1996_03
Patent number
US05502044

Reaction notes

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