Iodine → 5(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-(4-iodophenyl)oxazolidin-2-one

HRID 1167496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167496
[I:1]I.[S:3]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]2[O:14][C:13](=[O:15])[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11]2)=[N:4]1>C(#N)C.C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[S:3]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]2[O:14][C:13](=[O:15])[N:12]([C:16]3[CH:17]=[CH:18][C:19]([I:1])=[CH:20][CH:21]=3)[CH2:11]2)=[N:4]1

Komponenten

6

Edukt 2

HCID 807IodineHCID 699806285(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-phenyloxazolidin-2-one

Produkt 1

HCID 699805285(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-(4-iodophenyl)oxazolidin-2-oneAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 76299Silver trifluoroacetateKatalysatorHCID 6212ChloroformLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Iodine (0.67 g, 2.64 mmol) was added portionwise to a stirred solution of 5(R)-1,2,5-thiadiazol-3-yloxymethyl-3-phenyloxazolidin-2-one (0.7 g, 2.53 mmol) and silver trifluoroacetate (0.727 g, 3.29 mmol) in acetonitrile (4 ml) and chloroforrn (6 ml). The mixture was stirred for 24 hours in the dark. The mixture was filtered and the filtrate evaporated. The residue was extracted with EtOAc and the extract washed with water, dilute ammonia (0.1 ml of 0.88SG ammonia in 25 ml water), water and brine, dried (Na2SO4) and evaporated to give the title product as a solid (0.749 g, 73%)

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. extractionThe residue was extracted with EtOAc
  4. washthe extract washed with water, dilute ammonia (0.1 ml of 0.88SG ammonia in 25 ml water), water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-69288cb7e31449a7bc7378ee776070a1
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06617339B1

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