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Sodium Iodide → N'-Desaminomethylsulfonyl-N'-nitryl Dofetilide

HRID 1032668
Notes
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Reaction equation

HRID 1032668 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH3:14][S:15]([NH:18][C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25]Cl)=[CH:21][CH:20]=1)(=[O:17])=[O:16].C(=O)(O)[O-].[Na+].[I-].[Na+]>C(#N)C>[CH3:14][S:15]([NH:18][C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25][N:2]([CH3:1])[CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)=[CH:21][CH:20]=1)(=[O:17])=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 2794239N-methyl-4-nitrophenethylamineHCID 20086989N-[4-(2-Chloroethoxy)phenyl]-methanesulfonamide

Product 1

HCID 19915717N'-Desaminomethylsulfonyl-N'-nitryl DofetilideYield 38.1%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A suspension of N-methyl-4-nitrophenethylamine (1.1 g), 2-(4-methanesulphonamidophenoxy)ethyl chloride (1.5 g), sodium bicarbonate (0.5 g) and sodium iodide (0.9 g) in acetonitrile (100 ml) was stirred at reflux for 4 days. On evaporation to dryness the resultant oil was partitioned between 2N aqueous sodium bicarbonate solution and methylene chloride. After two further extractions with methylene chloride, the organic portions were combined, washed with saturated brine solution, dried over anhydrous magnesium sulphate, filtered and evaporated to dryness. The resultant brown oil was chromatographed on silica ("Kieselgel 60"-Trade Mark) eluting with ethyl acetate followed by collection and evaporation of suitable fractions to give the title compound as a yellow solid, (0.9 g).

Workup

  1. temperatureat reflux for 4 days
  2. customOn evaporation to dryness the resultant oil
  3. customwas partitioned between 2N aqueous sodium bicarbonate solution and methylene chloride
  4. extractionAfter two further extractions with methylene chloride
  5. washwashed with saturated brine solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe resultant brown oil was chromatographed on silica ("Kieselgel 60"-Trade Mark)
  10. washeluting with ethyl acetate
  11. customfollowed by collection and evaporation of suitable fractions

Sources & evidence

ORD record
ord-4f456bd799d14cb0afa6be7ae62af19b
Source dataset
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04959366

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes