Methanol → 1-Naphthalen-2-yl-imidazolidin-2-one

HRID 2383788

Reaktionsgleichung

Reaktionsgleichung von HRID 2383788
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)=[O:6].[H-].[Na+].CO>CN(C=O)C.C1COCC1.C(Cl)(Cl)Cl>[CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[N:7]1[CH2:2][CH2:3][NH:4][C:5]1=[O:6]

Komponenten

7

Edukt 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 256650Urea, 1-(2-chloroethyl)-3-(2-naphthyl)-

Produkt 1

HCID 596361671-Naphthalen-2-yl-imidazolidin-2-oneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-(2-Chloro-ethyl)-3-naphthalen-2-yl-urea (I-79a: 750 mg, 3.01 mmol) in dry DMF (10 mL) was added to a stirred solution of sodium hydride (150 mg, 3.1 mmol) in THF (10 mL) at 0° C. The reaction temperature was maintained at room temperature for 30 minutes. The reaction was monitored by TLC (5% MeOH in chloroform, double run). The reaction mixture was quenched with MeOH at 0° C., concentrated under reduced pressure and partitioned between ice water and chloroform. The organic layer was dried over Na2SO4, and concentrated under reduced pressure to afford 600 mg (94% yield) of 1-naphthalen-2-yl-imidazolidin-2-one.

Aufarbeitung

  1. customThe reaction mixture was quenched with MeOH at 0° C.
  2. concentrationconcentrated under reduced pressure
  3. custompartitioned between ice water and chloroform
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-147c786f8e224fc7a174188866e20021
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263635B2

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