Triethylamine → N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}thien-2-ylsulfonamide

HRID 413020

Reaktionsgleichung

Reaktionsgleichung von HRID 413020
C(N(CC)CC)C.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[S:13](Cl)(=[O:15])=[O:14].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[N:25]2[CH2:28][CH:27]([NH2:29])[CH2:26]2)=[CH:20][CH:19]=1>ClCCl>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[N:25]2[CH2:26][CH:27]([NH:29][S:13]([C:9]3[S:8][CH:12]=[CH:11][CH:10]=3)(=[O:15])=[O:14])[CH2:28]2)=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 218965981-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamine

Produkt 1

HCID 9955542N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}thien-2-ylsulfonamideAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

69.3 mm3 of triethylamine and 110 mg of thien-2-ylsulfonyl chloride are successively added, at room temperature and under an argon atmosphere, to a solution of 61.4 mg of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine in 3 cm3 of dichloromethane. After stirring for 68 hours at room temperature, the reaction mixture is introduced into a Bond Elut® SCX cartridge (3 cm5/500 mg) , eluting successively with twice 2 cm3 of dichloromethane and then twice 2 cm3 of a 1 M solution of ammonia in methanol. The ammoniacal fractions are pooled and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is dissolved in 5 cm3 of dichloromethane, washed with three times 3 cm3 of distilled water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). 60 mg of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}thien-2-ylsulfonamide are thus obtained in the form of a cream-colored foam [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 2.77 (split t, J=7 and 2 Hz: 2H); 3.40 (split t, J=7 and 2 Hz: 2H); 4.06 (mt: 1H); 4.21 (s: 1H); from 4.85 to 5.25 (broad unresolved complex: 1H); 7.06 (t, J=4.5 Hz: 1H); from 7.15 to 7.35 (mt: 8H); 7.58 (mt: 2H)].

Aufarbeitung

  1. additionthe reaction mixture is introduced into a Bond Elut® SCX cartridge (3 cm5/500 mg)
  2. washeluting successively with twice 2 cm3 of dichloromethane
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue obtained
  5. washwashed with three times 3 cm3 of distilled water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-c3a324cd0876416991f4a5b512499a88
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566356B2

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