Water → N-[2-(6-methyl-2-pyridyl)ethyl]-4-(N-acetyl-N-methylamino)benzenesulfonamide

HRID 1198647

Reaction equation

HRID 1198647 reaction equation
C[NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1.[C:12]([N:15]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)[CH3:16])(=[O:14])[CH3:13].C([O-])(=O)C.[Na+].O>C(O)C>[CH3:11][C:7]1[N:6]=[C:5]([CH2:4][CH2:3][NH:2][S:23]([C:20]2[CH:19]=[CH:18][C:17]([N:15]([C:12](=[O:14])[CH3:13])[CH3:16])=[CH:22][CH:21]=2)(=[O:25])=[O:24])[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2931464-(N-methylacetamido)benzene-1-sulfonyl chlorideHCID 517045Sodium AcetateHCID 13400642Methyl[2-(6-methylpyridin-2-yl)ethyl]amine

Product 1

HCID 22918888N-[2-(6-methyl-2-pyridyl)ethyl]-4-(N-acetyl-N-methylamino)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Methyl-N-[2-(6-methyl-2-pyridyl)ethyl]amine (14.66 g, 97.7 mmol) was added to a suspension of the 4-(N-acetyl-N-methylamino)benzenesulfonyl chloride (24.2 g, 97.3 mmol) prepared in Preparative Example 12 and sodium acetate (24.0 g) in ethanol (140 ml). The obtained mixture was stirred at room temperature overnight, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of common salt, dried over magnesium sulfate, and concentrated to give N-[2-(6-methyl-2-pyridyl)ethyl]-4-(N-acetyl-N-methylamino)benzenesulfonamide as a colorless oil. This oil was dissolved in 4N aqueous hydrochloric acid. The solution was heated under reflux for 2 hours. The pH of the mixture was adjusted to about 8 by the addition of an aqueous solution of sodium hydrogencarbonate. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of common salt, dried over magnesium sulfate, and concentrated to give an oily residue. This residue was purified by flash column chromatography (chloroform/methanol/aqueous ammonia=97:3:0.3) to give the title compound as a light brown oil (25.8 g, overall yield of two steps: 83%).

Workup

  1. extractionThe obtained mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-324cfdd41f5d4c889bf985efd0ad049c
Source dataset
uspto-grants-1994_01
Patent number
US05281626

Linked notes

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