Lithium iodide → 3-[(Dipropylamino)carbonyl]-5-(5-methyl-1,2,4-oxadiazol-3-yl)benzoic Acid

HRID 348852

Reaktionsgleichung

Reaktionsgleichung von HRID 348852
[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:6])[CH2:2][CH3:3].[I-].[Li+]>N1C=CC=CC=1>[CH2:23]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:6])[CH2:24][CH3:25]

Komponenten

4

Edukt 2

HCID 66321Lithium iodideHCID 21086176Methyl 3-[(dipropylamino)carbonyl]-5-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate

Produkt 1

HCID 210857883-[(Dipropylamino)carbonyl]-5-(5-methyl-1,2,4-oxadiazol-3-yl)benzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A stirred solution of methyl 3-[(dipropylamino)carbonyl]-5-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate (629 mg, 1.8 mmol) and lithium iodide (2.4 g, 18 mmol) in pyridine (7 ml) is refluxed for 18 h. The reaction mixture is cooled to room temperature and the solvent is concentrated under reduced pressure. The residue is dissolved in water, washed with ethyl acetate, the aqueous layer is acidified to pH 3 with 1 N hydrochloric acid and extracted with chloroform (3×100 mL). The organic layer is dried (sodium sulfate), filtered, and concentrated to give the title compound. 1H NMR (500 MHz, CDCl3) δ 11.11 (br s, 1H), 8.85 (t, J=1 Hz, 1H), 8.31 (t, J=1 Hz, 1H), 8.23 (t, J=1 Hz, 1H), 3.51 (s, 2H), 3.19 (s, 2H), 2.72 (s, 3H), 1.73 (d, J=7 Hz, 2H), 1.56 (d, J=7 Hz, 2H), 1.01 (t, J=7 Hz, 3H), 0.76 (t, J=7 Hz, 3H).

Aufarbeitung

  1. concentrationthe solvent is concentrated under reduced pressure
  2. dissolutionThe residue is dissolved in water
  3. washwashed with ethyl acetate
  4. extractionextracted with chloroform (3×100 mL)
  5. dry with materialThe organic layer is dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cda1058f98504dea9fa59d25292931c8
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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