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Chloroform → (+/-)-6-Fluoro-8-amino-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione

HRID 279877
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 279877
[F:1][C:2]1[CH:3]=[C:4]([N+:18]([O-])=O)[C:5]2[O:17][CH2:16][CH2:15][C:8]3([S:12][C:11](=[O:13])[NH:10][C:9]3=[O:14])[C:6]=2[CH:7]=1.C(Cl)(Cl)Cl>C(O)C.[Pt]=O>[F:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]2[O:17][CH2:16][CH2:15][C:8]3([S:12][C:11](=[O:13])[NH:10][C:9]3=[O:14])[C:6]=2[CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6212ChloroformHCID 13998517(+/-)-6-fluoro-8-nitro-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione

Produkt 1

HCID 13998518(+/-)-6-Fluoro-8-amino-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)Katalysator2×HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

755 mg of (±)-6-fluoro-8-nitro-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione were hydrogenated at room temperature and normal pressure in the presence of 50 mg of platinum oxide in 50 ml of ethanol. An additional 100 mg of platinum oxide were added after 30 minutes. After 2.5 hours under hydrogen, some chloroform was added, the catalyst was filtered, the filtrate was concentrated and the residue was chromatographed on silica gel 60 with chloroform/methanol (19:1). (±)-6-Fluoro-8-amino-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione was obtained in the form of a yellowish foam. The IR spectrum showed amine bands at 3383, 3202 and 2766 cm-1, in the mass spectrum the molecular ion appeared as a basic peak (m/e=268).

Aufarbeitung

  1. customwere hydrogenated at room temperature
  2. filtrationthe catalyst was filtered
  3. concentrationthe filtrate was concentrated
  4. customthe residue was chromatographed on silica gel 60 with chloroform/methanol (19:1)

Quellen und Nachweise

ORD-Eintrag
ord-a831adcd33fc473cbbe22694fcff8ece
Quelldatensatz
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04587256

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