Ethanesulfonyl chloride → HCID 9910756, compound

HRID 1267968Notes

Reaction equation

HRID 1267968 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[NH2:22])=[CH:10][CH:9]=[CH:8][N:7]=1.[CH2:26]([S:28](Cl)(=[O:30])=[O:29])C>C(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[NH:22][S:28]([CH3:26])(=[O:30])=[O:29])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 9885020HCID 9885020, compound

Product 1

HCID 9910756HCID 9910756, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

2-(3-Chlorophenoxy)-3-[3-(3-aminopyridin-4-yl)propoxy]pyridine (0.15 g, 0.42 mmol) obtained in Example 25 is dissolved in methylene chloride (5 ml) and pyridine (0.34 ml), and thereto is added ethylsulfonyl chloride (0.04 ml, 0.50 mmol) under ice-cooling, and the mixture is stirred for 3 hours. To the mixture is added ice-water (20 ml), and the mixture is extracted with ethyl acetate (50 ml×2). The organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution (20 ml×2) and a saturated brine (20 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by basic silica gel column chromatography (eluent: chloroform/methanol), and further recrystallized from diethyl ether to give the title compound (0.07 g) as colorless crystals, m.p. 131-133° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with ethyl acetate (50 ml×2)
  3. washThe organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution (20 ml×2)
  4. dry with materiala saturated brine (20 ml×2), dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by basic silica gel column chromatography (eluent: chloroform/methanol)
  7. customfurther recrystallized from diethyl ether

Sources & evidence

ORD record
ord-39042bda0694406db5c532d02eb967f8
Source dataset
uspto-grants-2003_04
Patent number
US06555557B1

Reaction notes

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