Sodium Dithionite → HCID 86598609, compound

HRID 1817123Notes

Reaction equation

HRID 1817123 reaction equation
[CH:1](/[CH:9]([S:19]([CH:22](/[CH:32]=[CH:33]/[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=1)(=[O:21])=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.NN.[H][H].[O-]S(S([O-])=O)=O.[Na+].[Na+]>[Pd]>[CH:1](/[CH:9]([S:19]([CH:22](/[CH:32]=[CH:33]/[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=1)(=[O:21])=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)=[CH:2]\[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 24489Sodium DithioniteHCID 24654Hydrazine hydrate (1:1)HCID 86598610HCID 86598610, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86598609HCID 86598609, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

According to the Scheme 1 below, the benzyl thioacetic acid C is formed by the reaction of sodium thioglycollate and a benzyl halide B. The benzyl thioacetic acid C is then oxidized with 30% hydrogen peroxide to give a corresponding benzylsulfonyl acetic acid D. Condensation of the benzylsulfonyl acetic acid D with an aromatic aldehyde E via a Knoevenagel reaction in the presence of benzylamine and glacial acetic acid yields the desired (E)-styryl-3-nitrobenzylsulfone F. The (E)-styryl-3-nitrobenzylsulfone F is then reduced via either palladium catalyzed hydrogenation with hydrazine hydrate as the hydrogen source or with Na2S2O4, and subsequently alkylated to give the desired (E)-styryl-3-aminobenzylsulfone IIIa.

Sources & evidence

ORD record
ord-1f68a599079f451b82aeffaaafa5cda0
Source dataset
uspto-grants-2009_10
Patent number
US07598232B2

Reaction notes

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