Morpholine → 4-((3-Bromophenyl)sulphonyl)morpholine

HRID 45000

Reaktionsgleichung

Reaktionsgleichung von HRID 45000
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:9]=[C:10]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([S:14]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 8083MorpholineHCID 17943m-Bromobenzenesulphonyl chloride

Produkt 1

HCID 36960024-((3-Bromophenyl)sulphonyl)morpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Morpholine (0.19 mL, 0.0022 mol) in 1.0 ml of THF was added dropwise to a solution of 3-bromobenzenesulfonyl chloride (0.3 mL, 0.002 mol) and TEA (0.30 mL, 0.0022 mol) in dry 4.0 mL of THF cooled in an ice bath. The reaction mixture was stirred overnight at room temperature and was then partitioned between 0.05N HCl and ethyl acetate. The organic layer was washed with water (2×), and brine (1×), and was then dried over anhydrous magnesium sulfate, filtered and then was concentrated in vacuo to give 4-[(3-bromophenyl)sulfonyl]morpholine as a white crystalline product (470 mg, 78%). LCMS (M+H)+: m/z=306, 308.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customwas then partitioned between 0.05N HCl and ethyl acetate
  3. washThe organic layer was washed with water (2×), and brine (1×)
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationwas concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-97b2dbb0c3a74f338a7b568d5b6b8ee7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541425B2

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