Hydrochloric Acid → (S)-4-{4-[2-(3-cyanopropylidene)hydrazino]benzyl}-1,3-oxazolidin-2-one

HRID 1608998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1608998
Cl.Cl.[NH:3]([C:5]1[CH:17]=[CH:16][C:8]([CH2:9][C@H:10]2[CH2:14][O:13][C:12](=[O:15])[NH:11]2)=[CH:7][CH:6]=1)[NH2:4].C(O[CH:21](OCC)[CH2:22][CH2:23][C:24]#[N:25])C>O>[C:24]([CH2:23][CH2:22][CH:21]=[N:4][NH:3][C:5]1[CH:17]=[CH:16][C:8]([CH2:9][C@H:10]2[CH2:14][O:13][C:12](=[O:15])[NH:11]2)=[CH:7][CH:6]=1)#[N:25]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 876164,4-DiethoxybutanenitrileHCID 45356867(S)-4-(4-Hydrazinylbenzyl)oxazolidin-2-one hydrochloride

Produkt 1

HCID 70196055(S)-4-{4-[2-(3-cyanopropylidene)hydrazino]benzyl}-1,3-oxazolidin-2-oneAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1M aqu. HCl (4.0 ml) was added to a solution of the product from step (a) (2.4 g) in water (35 ml). 3-Cyanopropanal diethylacetal (Aldrich, 1.7 g) was added at room temperature and the mixture stirred for 2 hours. Further acetal (0.20 g) was added and the mixture stirred for another 20 minutes. The aqueous phase was decanted from the resulting gum and extracted with ethyl acetate. The extracts were combined with the gum and evaporated in vacuo to give the desired product (2.5 g).

Aufarbeitung

  1. stirringthe mixture stirred for another 20 minutes
  2. customThe aqueous phase was decanted from the resulting gum
  3. extractionextracted with ethyl acetate
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a1f05403e726463cafaae926fe105115
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05399574

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