2-Thiophenesulfonamide → HCID 67332485, Verbindung

HRID 1258376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258376
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=O)[CH:4]=[C:3]1[S:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[S:25]([NH2:28])(=[O:27])=[O:26]>Cl[Ti](Cl)(Cl)Cl.C(N(CC)CC)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[N:28][S:25]([C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)(=[O:27])=[O:26])[CH:4]=[C:3]1[S:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Komponenten

5

Edukt 2

HCID 728812-ThiophenesulfonamideHCID 13813614Ethyl [(1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetate

Produkt 1

HCID 67332485HCID 67332485, VerbindungAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

63 mg (0.228 mmoles) ethyl 2-(1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)acetate (7a) was mixed with 37 mg (0.228 mmoles) thiophene-2-sulfonamide in 2.5 ml dichloromethylene, to which at 0° C. was added 76 mg TiCl4.2THF followed by 70 μl triethylamine. The mixture was heated at 60° C. with microwave synthesizer (Initiator 8, Biotage) for 20 min. Diluted with dichloromethylene to 60 ml, the reaction mixture was washed with H2O and brine and dried over Na2SO4. After removal of Na2SO4, the filtrate was concentrated and the residue was purified with flash column (EtOAc/Hexane) affording title compound 58 mg (60.4%) as orange oil which was solidified on standing, m.p.: 110-112° C.

Aufarbeitung

  1. additionDiluted with dichloromethylene to 60 ml
  2. washthe reaction mixture was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. customAfter removal of Na2SO4
  5. concentrationthe filtrate was concentrated
  6. customthe residue was purified with flash column (EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d76036d48da34be1a5b70effc8745b28
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466157B2

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