Sodium Dithionite → Ethyl 2-(1-hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-ylthio)acetate

HRID 1258377Notes

Reaction equation

HRID 1258377 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)/[C:5](=[N:12]/[S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])/[CH:4]=[C:3]1[S:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[O-]S(S([O-])=O)=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][C:3]=1[S:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 58398202ethyl 2-[(4E)-1-oxo-4-thiophen-2-ylsulfonyliminonaphthalen-2-yl]sulfanylacetate

Product 1

HCID 44608823Ethyl 2-(1-hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-ylthio)acetateYield 58.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

52 mg (E)-ethyl 2-(1-oxo-4-(thiophen-2-ylsulfonylimino)-1,4-dihydronaphthalen-2-ylthio)acetate (8a) was dissolved in 2 ml THF, to which was added 2 ml aqueous solution containing 107 mg Na2S2O4. The resulting biphasic solution was stirred at r.t. for 1 h until it turned pale yellow. The mixture was diluted with ethyl acetate and washed with water and brine. Dried over Na2SO4, the organic solution was filtered and the filtrate was concentrated. The crude product was purified via flash column (EtOAc/Hexane) yielding 25.2 mg (58.7%) title compound, m.p.: 116-118° C.

Workup

  1. washwashed with water and brine
  2. dry with materialDried over Na2SO4
  3. filtrationthe organic solution was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified via flash column (EtOAc/Hexane)

Sources & evidence

ORD record
ord-78c9985802c04604ac721cd6df58bf3f
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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