Methyl 4-(chloromethyl)benzoate → Methyl 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin4-yl)methyl)benzoate

HRID 1180112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180112
[CH3:1][N:2]1[C:6](=[O:7])[NH:5][C:4](=[O:8])[NH:3]1.[Na].[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1>CS(C)=O>[CH3:1][N:2]1[C:6](=[O:7])[N:5]([CH2:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([O:11][CH3:10])=[O:21])=[CH:14][CH:15]=2)[C:4](=[O:8])[NH:3]1

Komponenten

5

Edukt 3

HCID 36664Methyl 4-(chloromethyl)benzoateHCID 1792121-Methyl-1,2,4-triazolidine-3,5-dioneHCID 5360545Sodium

Produkt 1

HCID 58978277Methyl 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin4-yl)methyl)benzoateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 1-methyl-[1,2,4]triazolidine-3,5-dione (1.886 g, 0.0164 mol) and sodium hyhride (200 mg) in DMSO (5 mL) was added 4-chloromethyl-benzoic acid methyl ester (1.0 g, 0.0054 mol). The mixture was stirred at RT for overnight, quenched with H2O (100 mL), and extracted by CH2Cl2. The organic layer was washed with H2O, dried (Na2SO4) and concentrated in vacuo to yield methyl 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin4-yl)methyl)benzoate (1.02 g, 72%). 1H NMR (CDCl3): 7.93 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 4.68 (s, 2H), 3.83 (s, 3H), 3.27 (s, 3H). MS (ESI) m/e: 264 (M++1)

Aufarbeitung

  1. customquenched with H2O (100 mL)
  2. extractionextracted by CH2Cl2
  3. washThe organic layer was washed with H2O
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b1ba69038d7549e4a387c422e77bffbb
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279576B2

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