Sodium Methoxide → HCID 10832243, compound

HRID 2287393Notes

Reaction equation

HRID 2287393 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13]([NH:16][C:17]1[N:18]=[N:19][C:20](Cl)=[CH:21][CH:22]=1)(=[O:15])=[O:14].[CH3:25][O-:26].[Na+]>CN1CCCC1=O.CO>[CH3:1][N:2]([CH3:24])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13]([NH:16][C:17]1[N:18]=[N:19][C:20]([O:26][CH3:25])=[CH:21][CH:22]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 11793037HCID 11793037, compound

Product 1

HCID 10832243HCID 10832243, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-Dimethylamino-N-(6-chloro-3-pyridazinyl)-1-naphthalenesulphonamide (0.36 g), was suspended in N-methylpyrrolidone (1 ml) and freshly prepared 1M sodium methoxide in methanol (3 ml) was added. The reaction mixture was heated to reflux for 4 hours, cooled and evaporated to dryness. The residue was purified by flash chromatography on silica gel (5 g) eluting with a methanol/dichloromethane gradient to give 5-dimethylamino-N-(6-methoxy-3-pyridazinyl)-1-naphthalenesulphonamide (0.14 g), m.p. 125-127° C.; mass spectrum (+ve CI): 359 (M+N)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperaturecooled
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography on silica gel (5 g)
  6. washeluting with a methanol/dichloromethane gradient

Sources & evidence

ORD record
ord-5f40f052955e435089fc096b3c92a06e
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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