Chlorosulfamic acid → 2-Sulfamoylamino-6-(2-methylprop-1-enyl)benzonitrile
Reaktionsgleichung
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[C:11]([CH3:13])[CH3:12])[C:3]=1[C:4]#[N:5].[S:14](Cl)(=[O:17])(=[O:16])[NH2:15]>CN(C)C(=O)C>[S:14]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[C:11]([CH3:13])[CH3:12])[C:3]=1[C:4]#[N:5])(=[O:17])(=[O:16])[NH2:15]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 2-amino-6-(2-methylprop-1-enyl)benzonitrile (Example 129b) (1.24 g; 7.23 mmol) in N,N-dimethylacetamide (DMA) (20.0 mL), under a nitrogen atmosphere, was treated with sulfamoyl chloride (1.67 g; 14.45 mmol) at room temperature. The obtained mixture was stirred at room temperature for 2 h and the reaction was quenched with water (40 mL). The mixture was extracted with EtOAc (4×80 mL), the combined extract was washed with water (2×20 mL) and brine, and dried with MgSO4. The filtrate was evaporated and the residue was purified by chromatography on silica gel using gradient (Hexanes/EtOAc 1:0 to 1:1), to give 1.69 g (93%) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ9.42 (broad s, 1H), 7.61 (t, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.24 (broad s, 2H), 7.19 (d, J=8.0 Hz, 1H), 6.35 (broad s, 1H), 1.92-1.95 (m, 3H), 1.76-1.79 (m, 3H).