反应详情

A solution of 50 g (0.276 mole) of ethyl 1,4-dimethyl-1H-pyrrole-2-acetate and 64 g (0.303 mole) of 2,4-dichlorobenzoyl chloride in 310 mL of xylene was heated under reflux for 4 h under argon. After cooling, a 20% solution of 3-dimethylaminopropylamine in H2O was added and stirred one hour. The organic layer was washed twice with 1N HCl, water, brine, and dried (MgSO4). Evaporation of the solvent in vacuo gave a solid which was recrystallized from methanol to give 79.39 g of product: mp 90°-92° C.; mass spectrum (Cl--CH4) m/z=354 (M+1); NMR 300 MHz (CDCl3) d 7.5 (s, 1H); 7.3 (dd, 2H); 6.0 (s, 1H); 4.2 (q, 2H); 3.9 (s, 3H); 3.65 (s, 2H); 1.6 (s, 3H); 1.25 (t, 3 H). Anal Calcd for C17H17Cl2NO3 : C, 57.64; H, 4.84; N, 3.95. Found: C, 57.52; H, 4.60; N, 3.80.

1. temperatureunder reflux for 4 h under argon
2. temperatureAfter cooling
3. washThe organic layer was washed twice with 1N HCl, water, brine
4. dry with materialdried (MgSO4)
5. customEvaporation of the solvent in vacuo
6. customgave a solid which
7. customwas recrystallized from methanol