Pyridine → N-(3-bromo-4-methylphenyl)-N-(2,2-diethoxyethyl)benzenesulfonamide

HRID 221923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221923
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:13]=[C:14]([NH:19][CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])[CH:15]=[CH:16][C:17]=1[CH3:18].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[Br:11][C:12]1[CH:13]=[C:14]([N:19]([CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])[S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:15]=[CH:16][C:17]=1[CH3:18]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 59488813(3-Bromo-4-methylphenyl)-(2,2-diethoxyethyl)-amine

Produkt 1

HCID 59488771N-(3-bromo-4-methylphenyl)-N-(2,2-diethoxyethyl)benzenesulfonamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under a nitrogen stream, benzenesulfonyl chloride (3.12 mL g, 24.48 mmol) was added dropwise under ice cooling to a mixture of (3-bromo-4-methylphenyl)-(2,2-diethoxyethyl)-amine (4.91 g, 16.25 mmol), pyridine (10.1 mL, 124.88 mmol) and dichloromethane (41 mL), and the resultant mixture was then stirred at the same temperature for 1 hour. After stirring at room temperature for 2 hours, the reaction mixture was added to saturated aqueous sodium hydrogen carbonate. The resultant mixture was extracted with dichloromethane. The organic layer was washed with 5% aqueous hydrochloric acid and dried (anhydrous potassium carbonate). Solvent was then removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:4)), to thereby obtain the titled compound (5.94 g, 83%).

Aufarbeitung

  1. extractionThe resultant mixture was extracted with dichloromethane
  2. washThe organic layer was washed with 5% aqueous hydrochloric acid
  3. dry with materialdried (anhydrous potassium carbonate)
  4. customSolvent was then removed by distillation under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:4))

Quellen und Nachweise

ORD-Eintrag
ord-d6bbd0b0e5724ba989f8c2ce694e84a4
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207134B2

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