4-Aminobenzamide → 4-amino-N-(3,5-dimethylphenyl)benzamide
Reaktionsgleichung
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.I[C:12]1[CH:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[CH:17]=1>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:8][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=2)=[O:7])=[CH:4][CH:3]=1Komponenten
3
Versuchsvorschrift
Using general procedure A, 4-aminobenzamide (170 mg, 1.25 mmol) was coupled with 5-iodo-m-xylene (150 μL, 1.04 mmol). The crude product was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 2:3; 15 in L fractions). Fractions 9–18 provided 246 mg (98% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.74–7.69 (m, 2H), 7.66 (br s, 1H), 7.28 (s, 2H), 6.78 (s, 1H), 6.74–6.69 (m, 2H), 4.05 (br s, 2H), 2.33 (s, 6H). 13C NMR (100 MHz, CDCl3): δ 165.7, 150.3, 139.1, 138.6, 129.2, 126.2, 124.8, 118.2, 114.6, 21.8.
Aufarbeitung
- customThe crude product was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 2:3; 15 in L fractions)