Sulfuric Acid → 5-(3-(3-Morpholinopropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamide
Reaktionsgleichung
[C:1]([C:3]1[C:4]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[N:5][S:6][C:7]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:10])#[N:2].[OH:30]S(O)(=O)=O>>[N:15]1([CH2:14][CH2:13][CH2:12][NH:11][C:9]([NH:8][C:7]2[S:6][N:5]=[C:4]([C:21]3[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)[C:3]=2[C:1]([NH2:2])=[O:30])=[O:10])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1Komponenten
3
Reaktionsbedingungen
- Temperatur
- 45 °C
Versuchsvorschrift
A mixture of 1-(4-cyano-3-(4-nitrophenyl)isothiazol-5-yl)-3-(3-morpholinopropyl)urea (113 mg, 0.27 mmol) in 3.5 mL conc. H2SO4 was heated at 45° C. After 1.5 hours the reaction was quenched into 100 mL ice water giving a white gel-like solid. The aqueous solution was made basic using Na2CO3 and then extracted with EtOAc, the EtOAc layer washed with brine, dried with anhydrous Na2SO4 and rotary evaporated giving the title compound as a light beige solid (118 mg, 100%).