Benzenesulfonyl chloride → 3-(2-Tert-butylphenoxy)-1-(phenylsulfonyl)azetidine

HRID 2041976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2041976
[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH:8]1[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([S:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:24])=[O:23])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 534095303-(2-Tert-butylphenoxy)azetidine

Produkt 1

HCID 595773173-(2-Tert-butylphenoxy)-1-(phenylsulfonyl)azetidineAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(2-tert-butylphenoxy)azetidine (0.30 g, 1.46 mmol) in pyridine (5.0 mL) was added benzenesulfonyl chloride (0.28 g, 1.61 mmol). After stirring for 16 h at room temperature, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. The organic layer was washed with 1.0 N hydrochloric acid, water, saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting yellow solid was recrystallized from heptane/ethyl acetate to provide 3-(2-tert-butylphenoxy)-1-(phenylsulfonyl)azetidine (0.29 g, 57%) as a pale brown powder.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with 1.0 N hydrochloric acid, water, saturated sodium chloride
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting yellow solid was recrystallized from heptane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5ef943e2899746cdaeedcbc1c7011ce7
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586571B2

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