2,4-Dichlorobenzenemethanethiol → 17alpha-(2',4'-Dichlorobenzylthio)-1,4-Androstadiene-3,11-Dione

HRID 2052257Notes

Reaction equation

HRID 2052257 reaction equation
[Na].[Cl:2][C:3]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:4]=1[CH2:5][SH:6].CS(O[C@H:17]1[CH2:22][CH2:21][C@H:20]2[C@H:23]3[C@H:33]([C:34](=[O:36])[CH2:35][C@:18]12[CH3:19])[C@:31]1([CH3:32])[C:26](=[CH:27][C:28](=[O:37])[CH:29]=[CH:30]1)[CH2:25][CH2:24]3)(=O)=O>C(O)C>[Cl:2][C:3]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:4]=1[CH2:5][S:6][C@@H:17]1[CH2:22][CH2:21][C@H:20]2[C@H:23]3[C@H:33]([C:34](=[O:36])[CH2:35][C@:18]12[CH3:19])[C@:31]1([CH3:32])[C:26](=[CH:27][C:28](=[O:37])[CH:29]=[CH:30]1)[CH2:25][CH2:24]3

Participants

5

Reactant 3

HCID 957562,4-DichlorobenzenemethanethiolHCID 5360545SodiumHCID 5660910317beta-Methanesulfonyloxy-1,4-androstadiene-3,11-dione

Product 1

HCID 2280984717alpha-(2',4'-Dichlorobenzylthio)-1,4-Androstadiene-3,11-Dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.04 gm. of sodium metal dissolved in 80 ml. of ethanol is added 5.55 ml. of 2,4-dichlorobenzylmercaptan followed by 1.5 gm. of 17β-methanesulfonyloxy-1,4-androstadiene-3,11-dione. Heat at reflux for 76 hours under an atmosphere of nitrogen. In a manner similar to that described in Example 1E, isolate the title compound.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 76 hours under an atmosphere of nitrogen

Sources & evidence

ORD record
ord-881461ffd3e64bccb82e2f4be6df9e76
Source dataset
uspto-grants-1980_01
Patent number
US04183924

Reaction notes

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