Triethylamine → N-(1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-4-fluorophenylsulfonamide

HRID 413023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413023
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[N:27]2[CH2:30][CH:29]([NH2:31])[CH2:28]2)=[CH:22][CH:21]=1>ClCCl>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[N:27]2[CH2:28][CH:29]([NH:31][S:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH2:30]2)=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 218965981-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamine

Produkt 1

HCID 10298542N-(1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-4-fluorophenylsulfonamideAusbeute 38,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.214 g of 4-fluorophenylsulfonyl chloride and 0.28 cm3 of triethylamine are added, at room temperature under an argon atmosphere, to a solution of 0.307 g of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine in 10 cm3 of dichloromethane. After stirring for 16 hours at room temperature, the reaction mixture is washed with 10 cm3 of distilled water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by flash chromatography on silica gel [eluant: dichloromethane/ethyl acetate (100/0 to 95/5 by volume) gradient]. 0.18 g of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-4-fluorophenylsulfonamide is obtained in the form of a white foam [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 2.74 (broad t, J=7.5 Hz: 2H); 2.39 (broad t, J=7.5 Hz: 2H); 3.98 (mt: 1H); 4.20 (s: 1H); 4.79 (d, J=9 Hz: 1H); from 7.10 to 7.35 (mt: 10H); 7.86 (mt: 2H)].

Aufarbeitung

  1. washthe reaction mixture is washed with 10 cm3 of distilled water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue obtained
  6. customis purified by flash chromatography on silica gel [eluant: dichloromethane/ethyl acetate (100/0 to 95/5 by volume) gradient]

Quellen und Nachweise

ORD-Eintrag
ord-7376a1b4cb4f40fda491fc7e1a49b499
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566356B2

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