反应详情

To a stirred suspension of sodium hydride (0.2 g of 60%, 5 mmoles, washed with n-pentane) in DMF (10 ml) was added dropwise a solution of 4-amino-2-(butan-2-on-3-yl)oxy-5-chloro-N-[2-(diethylamino)ethyl]benzamide (1.78 g, 5 mmoles) in DMF (10 ml). After hydrogen evolution subsided, allyl bromide (690 mg, 5.7 mmoles) was added and the mixture stirred for 72 hours, followed by partition between water and methylene chloride. The organic phase was washed with water, dried and concentrated. The residue was chromatographed on deactivated silica, using methylene chloride (100), methanol (4), ammonia (0.5). The appropriate fractions were combined to give 0.58 g of crude product as a heavy oil. This was crystallized from ether to give the title compound as a white solid, mp 138°-140°. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ 8.24 (s, 1H); 8.0 (bs, 1H); 5.92 (s, 1H); 5.9-5.0 (m, 4H); 4.38 (bs, 2H); 3.58 (m, 2H); 3.0-2.3 (m, 8H); 2.28 (s, 3H); 1.62 (s, 3H); 1.04 (t, 6H).

1. customby partition between water and methylene chloride
2. washThe organic phase was washed with water
3. customdried
4. concentrationconcentrated
5. customThe residue was chromatographed on deactivated silica
6. customto give 0.58 g of crude product as a heavy oil
7. customThis was crystallized from ether