Cyanuric chloride → HCID 16638913, compound

Participants

Reaction Steps

A solution of 2,4,6-trichloro-1,3,5-triazine (0.66 g, 3.7 mmol) in acetone (16 ml) was poured onto ice water (35 ml) and added in small portions at 0° C. to (+/−)-norgalanthamine (1.0 g, 3.7 mmol). After the addition of 2N-sodium hydroxide (2 ml), the reaction mixture was refluxed for 40 hours. The aqueous phase was extracted with EtOAc (3×30 ml). The combined, organic phases were washed with common salt solution (30 ml), dried (Na2SO4) and concentrated by evaporation, to produce 0.90 g (59.5%) of compound 4e: 1H-NMR (CDCl3) δ 6.82 (d, J=10.0 Hz, 1H), 6.63 (d, J=10.0 Hz, 1H), 6.02 (b, 2H), 5.30 (d, J=11.0 Hz, 1H), 4.75 (d, J=16.0, 1H), 4.50 (b, 1H), 4.22 (d, J=11.0 Hz, 1H), 4.11 (b, 1H), 3.78 (s, 3H), 3.59 (m, 1H), 3.06 (m, 1H), 2.61 (d, J=16.0 Hz, 1H), 1.90 (m, 3H); 13C-NMR (CDCl3) δ 207.0 (s) 171.2 (s), 163.7 (s), 146.2 (s), 143.9 (s), 132.3 (d), 129.5 (s), 127.6 (s), 126.7 (d), 121.5 (d), 110.8 (d), 88.0 (d), 61.7 (d), 55.7 (q), 51.8 (t), 48.2 (5), 43.4 (t), 35.9 (t), 29.7 (t).

Provenance & Evidence