Pyridine → N-Benzyl-N-[3-(2-oxo-imidazolidin-1-yl)-phenyl]-benzenesulfonamide

HRID 386472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386472
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([N:15]2[CH2:19][CH2:18][NH:17][C:16]2=[O:20])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1>ClCCl>[CH2:1]([N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:19][CH2:18][NH:17][C:16]2=[O:20])[CH:10]=1)[S:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:29])=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 436966011-(3-Benzylamino-phenyl)-imidazolidin-2-one

Produkt 1

HCID 46182274N-Benzyl-N-[3-(2-oxo-imidazolidin-1-yl)-phenyl]-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-(3-benzylamino-phenyl)-imidazolidin-2-one (25 mg, 0.1 mmol), benzenesulphonyl chloride (39 μl, 31 mmol) and pyridine (27 μl, 34 mmol) in dry dichloromethane (1 ml) was heated to reflux for 15 hrs. The reaction mixture was then cooled to room temperature, quenched with water (10 ml) and extracted with dichloromethane (3×7 ml). The organic extracts were combined, dried (magnesium sulphate) and concentrated in vacuo. The crude residue was purified by preparative TLC (eluent 1:1 ethyl acetate:dichloromethane) to afford the title compound as a off white solid (9 mg, 24%). HPLC retention time 8.8 mins. Mass spectrum (ES+) m/z 425 (M+NH4).

Aufarbeitung

  1. temperatureto reflux for 15 hrs
  2. customquenched with water (10 ml)
  3. extractionextracted with dichloromethane (3×7 ml)
  4. dry with materialdried (magnesium sulphate)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative TLC (eluent 1:1 ethyl acetate:dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-bd628d5117d048588d53e99d988a9408
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372840B2

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