N,N'-Dimethylethylenediamine → Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate

HRID 1805360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805360
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[C:6]([Br:11])[CH:5]=1.[O:13]1[CH2:17][CH2:16][NH:15][C:14]1=[O:18].C(=O)([O-])[O-].[K+].[K+].CNCCNC>C(#N)C.[Cu]I>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([N:15]2[CH2:16][CH2:17][O:13][C:14]2=[O:18])[CH:7]=[C:6]([Br:11])[CH:5]=1

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 21942573Methyl 3-bromo-5-iodobenzoate

Produkt 1

HCID 67229228Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of 3-bromo-5-iodo-benzoic acid methyl ester (682 mg, 2 mmol), oxazolidin-2-one (191 mg, 2.2 mmol), CuI (76 mg, 0.4 mmol), potassium carbonate (545 mg, 4 mmol) and N,N′-dimethyl-ethane-1,2-diamine (86 uL, 0.8 mmol) in acetonitrile (15 mL) was stirred for 16 hours at 90° C. The precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford 3-bromo-5-(2-oxo-oxazolidin-3-yl)-benzoic acid methyl ester (480 mg, 80%) which was used for next step without further purification.

Aufarbeitung

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-76d820331c864ce989db863d5708d70c
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354443B2

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