反应详情

A mixture of N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-4-chlorobutan-amide (1.44 g, 0.004 mol) and piperidine (0.7 g, 0.8 ml, 0.008 mol) in toluene (50 ml) was heated under reflux for 3 h. The reaction mixture was cooled, poured into water and stirred. Toluene was separated dried and evaporated to give a crude product which was purified by repeated silica gel and neutral alumina column chromatography eluting with EtOAc/hexane (50:50 v/v) and CHCl3/hexane (80:20 v/v); mp 204-7° C., m/e 324, 78% (consistent with molecular formula C12H10BrN3OS, calcd. 324.20) 1H NMR CDCl3): δ 2.32-2.40 (m, 2H, —CH2), 2.76 (t, J=7.5 Hz, 2H, —CH2), 4.29 (t, J=7.5 Hz, 2H, —CH2), 7.62-7.84 (dd, J=8.5 Hz, 4H, ArH). 13C NMR: δ 18.3, 31.2, 47.9, 125.0, 128.7, 129.5, 132.3, 157.5, 162.9, 173.7.

1. temperaturewas heated
2. temperatureunder reflux for 3 h
3. temperatureThe reaction mixture was cooled
4. customToluene was separated
5. customdried
6. customevaporated