Methanol → 1-(3-Methyl-benzo[d]isoxazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383812
F[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:18]=3[CH3:19])[C:9]2=[O:20])=[CH:4][C:3]=1[C:21](=[N:23][OH:24])[CH3:22].[H-].[Na+].CO>CN(C=O)C.C(Cl)(Cl)Cl>[CH3:22][C:21]1[C:3]2[CH:4]=[C:5]([N:8]3[CH2:12][CH2:11][N:10]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][C:18]=4[CH3:19])[C:9]3=[O:20])[CH:6]=[CH:7][C:2]=2[O:24][N:23]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 866493961-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Produkt 1

HCID 498722501-(3-Methyl-benzo[d]isoxazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneAusbeute 14,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

1-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (220 mg, 0.670 mmol) in DMF (5 mL) was added to a stirred mixture of NaH (19 mg, 0.804 mmol) in DMF (2 mL) under nitrogen atmosphere at 0° C. The resulting mixture was stirred at room temperature for 21 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ethylacetate and ice water. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 28 mg of the product (14.5% yield).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethylacetate and ice water
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (1% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-6845d764a0294e1ba0fc8922f2518750
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263635B2

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