HCID 19915717, compound → Dofetilide Impurity 7

HRID 1032669Notes

Reaction equation

HRID 1032669 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:27]=[CH:26][C:9]([O:10][CH2:11][CH2:12][N:13]([CH3:25])[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[H][H]>C(O)C.[Ni]>[CH3:1][S:2]([NH:5][C:6]1[CH:27]=[CH:26][C:9]([O:10][CH2:11][CH2:12][N:13]([CH3:25])[CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 19915717HCID 19915717, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19915731Dofetilide Impurity 7Yield 72.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(4-methanesulphonamidophenoxy)-2-[N-methyl-N-(4-nitrophenethyl)amino]ethane (0.9 g) in ethanol (100 ml) was stirred for 16 hours at room temperature under three atmospheres of hydrogen in the presence of Raney Nickel ("Nicat 102"-Trade Mark). The reaction mixture was filtered and evaporated to dryness. The resultant solid was crystallised from toluene to give the title compound as yellow crystals, (0.6 g), m.p. 155°-157°.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. customThe resultant solid was crystallised from toluene

Sources & evidence

ORD record
ord-0aa4b28c280f4934b7ec1caa16052075
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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