Reaktionsgleichung
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH:19]([N:22]=[C:23]=S)([CH3:21])[CH3:20].C(N(CC)CC)C.C(Cl)(Cl)=O>CC(C)=O.C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:23]([NH:22][CH:19]([CH3:21])[CH3:20])=[N:12][S:9](=[O:11])(=[O:10])[C:3]=2[CH:4]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a suspension of 2-amino-5-bromobenzenesulfonamide (0.8 g; 3.2 mmol) and potassium carbonate (0.54 g; 3.9 mmol) in acetone (20 ml) was added isopropyl isothiocyanate (0.387 g; 3.84 mmol). The mixture was heated to 60° C. and after 16 hr cooled, concentrated in vacuo and the crude residue was taken up in tetrahydrofuran (50 ml) and cooled to 0° C. To the cooled mixture was added triethylamine (0.648 g; 6.4 mmol) followed by the addition of phosgene in toluene 1.9M (1.82 ml) over 2 min. After 1 hr at 0° C. the mixture was concentrated in vacuo. The crude product was taken up in water (10 ml) and pH was adjusted to 6 with sodium bicarbonate. The precipitated product was collected by filtration and dried in vacuo at 50° C. for 16 hr giving 390 mg (38.3%) of the title compound; m.p. >220° C.
Aufarbeitung
- temperaturecooled
- concentrationconcentrated in vacuo
- temperaturecooled to 0° C
- concentrationAfter 1 hr at 0° C. the mixture was concentrated in vacuo
- filtrationThe precipitated product was collected by filtration
- customdried in vacuo at 50° C. for 16 hr
Quellen und Nachweise
- ORD-Eintrag
- ord-c54c2f0a41d049fc9cc271ab922720e5
- Quelldatensatz
- uspto-grants-2001_06
- Patentnummer
- US06242443B1
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