反应详情

A solution of chloroarene 4 (20.57 g; 0.100 mol) in N-(2-aminoethyl)-acetamide (71.05 g; 0.696 mol) was heated from 60 to 120° C. over 20 min then kept at 120° C. for 4.0 h. After cooling to rt, the reaction was diluted with EtOAc (500 mL) then washed with water (1×150 mL). The aq phase was extracted with EtOAc (3×25 mL) and the combined organic portions were washed with water (2×25 mL) and saturated NaCl (2×50 mL). The solution was dried (MgSO4), filtered then concentrated in vacuo to 21.34 g of an off-white hard foam. The product was purified in two batches on silica gel (1.7 L total) using 15-8:1 DCM:MeOH yielding a hard white foam (15.36 g; 57%). LC (method B) tR=5.5 min; 1H NMR (200 MHz, CDCl3) δ 8.29 (m, 2H), 7.43 (m, 3H), 6.71 (brs, 1H), 5.41 (s, 1H), 5.12 (brt, J=5.4 Hz, 1H), 4.68 (brs, 2H), 3.53 (m, 1H), 3.45 (m, 1H), 1.83 (s, 3H); ESIMS 272.03 (100) [MH+].

1. washthen washed with water (1×150 mL)
2. extractionThe aq phase was extracted with EtOAc (3×25 mL)
3. washthe combined organic portions were washed with water (2×25 mL) and saturated NaCl (2×50 mL)
4. dry with materialThe solution was dried (MgSO4)
5. filtrationfiltered
6. concentrationthen concentrated in vacuo to 21.34 g of an off-white hard foam
7. customThe product was purified in two batches on silica gel (1.7 L total)