Water → HCID 18509276, compound

HRID 1356632Notes

Reaction equation

HRID 1356632 reaction equation
[H-].[Na+].[CH3:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[Cl:15][C:16]1[N:17]=[N:18][C:19](Cl)=[CH:20][CH:21]=1.O>CN(C=O)C>[Cl:15][C:16]1[N:17]=[N:18][C:19]([N:4]([CH3:3])[S:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)(=[O:7])=[O:6])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 24758Sodium hydrideHCID 673313,6-Dichloropyridazine

Product 1

HCID 18509276HCID 18509276, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.42 g (10.5 mmol)) in 10.0 ml of DMF, N-methyl-p-toluenesulfonamide (1.85 g (9.99 mmol)) was added under ice-cooling and with stirring. To the resulting mixture, after 15 minutes' stirring under cooling with ice, 3,6-dichloropyridazine (1.49 g (10.0 mmol)) was added. The reaction mixture was stirred at room temperature for one hour, poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was then subjected to silica gel column chromatography with ethyl acetate-hexane (1:3) as eluent, to give 1.41 g (47%) of the title compound as white crystals.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringTo the resulting mixture, after 15 minutes' stirring
  4. additionwas added
  5. stirringThe reaction mixture was stirred at room temperature for one hour
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water and saturated sodium chloride solution
  8. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a72c4e7d1164d7d9434aee10bf91bd2
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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