Iodine → 2-[2-(2-Pyridinyl)ethyl]-[1,3]dioxolo[4,5-g]-isothiazolo[4,5-c]quinolin-3(2H)-one

HRID 3271

Reaktionsgleichung

Reaktionsgleichung von HRID 3271
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]2[CH:16]=[C:17]3[O:25][CH2:24][O:23][C:18]3=[CH:19][C:20]=2[C:21]=1[SH:22])=[O:11].C(N(CC)CC)C.II>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][N:9]1[C:10](=[O:11])[C:12]2[CH:13]=[N:14][C:15]3[CH:16]=[C:17]4[O:25][CH2:24][O:23][C:18]4=[CH:19][C:20]=3[C:21]=2[S:22]1

Komponenten

5

Edukt 3

HCID 807IodineHCID 8471TriethylamineHCID 178418371HCID 178418371, Verbindung

Produkt 1

HCID 158956222-[2-(2-Pyridinyl)ethyl]-[1,3]dioxolo[4,5-g]-isothiazolo[4,5-c]quinolin-3(2H)-oneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To 4.1 g (0.012 mol) of 8-mercapto-[1,3]dioxolo [4,5-g]quinoline-7-carboxylic acid (2-pyridin-2-yl-ethyl)-amide (from Preparation 34) and 5 mL (0.035 mol) of triethylamine in 750 mL of methanol was added 2.95 g (0.012 mol) of iodine in 100 mL of methanol. The mixture was heated at reflux for 2 hours, cooled, and then concentrated to an oil. The residue was slurried in water, and the solid was collected and recrystallized in ethanol to give 3.5 g of the title compound, mp 200°-201° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated to an oil
  5. customthe solid was collected
  6. customrecrystallized in ethanol

Quellen und Nachweise

ORD-Eintrag
ord-612c475449ba4056a49ab5f66bcc7953
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733921

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