3,4-Dichlorotoluene-alpha-thiol → 17alpha-(3',4'-Dichlorobenzylthio)-1,4-Androstadiene-3,11-Dione

HRID 2052258Notes

Reaction equation

HRID 2052258 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][SH:6].CS(O[C@H:16]1[CH2:21][CH2:20][C@H:19]2[C@H:22]3[C@H:32]([C:33](=[O:35])[CH2:34][C@:17]12[CH3:18])[C@:30]1([CH3:31])[C:25](=[CH:26][C:27](=[O:36])[CH:28]=[CH:29]1)[CH2:24][CH2:23]3)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][S:6][C@@H:16]1[CH2:21][CH2:20][C@H:19]2[C@H:22]3[C@H:32]([C:33](=[O:35])[CH2:34][C@:17]12[CH3:18])[C@:30]1([CH3:31])[C:25](=[CH:26][C:27](=[O:36])[CH:28]=[CH:29]1)[CH2:24][CH2:23]3

Participants

3

Reactant 2

HCID 1189863,4-Dichlorotoluene-alpha-thiolHCID 5660910317beta-Methanesulfonyloxy-1,4-androstadiene-3,11-dione

Product 1

HCID 2280984917alpha-(3',4'-Dichlorobenzylthio)-1,4-Androstadiene-3,11-Dione

Procedure

In a manner similar to that described in Example 1A, 3,4-dichlorobenzylmercaptan is reacted with 17β-methanesulfonyloxy-1,4-androstadiene-3,11-dione to obtain the title compound of this example; m.p.=131°-133° C.; [α]D26 +150° (CHCl3); λmaxMeOH 228 nm (ε=26,000).

Sources & evidence

ORD record
ord-e824c6b4bdcf4cc7bfb9119c499cd750
Source dataset
uspto-grants-1980_01
Patent number
US04183924

Reaction notes

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