反应详情

温度

23 °C

A mixture of 3-(5-amino-4-ethylthio-3-indolyl)-1-propanol (0.93 g, 3.7 mmol), 3-chloro-4-methyl-1,2-dioxocyclobut-3-ene (0.58 g, 4.4 mmol) and Et3N (0.62 ml, 4.4 mmol) in DMF (50 ml) was stirred at 23° C. for 50 h before adding water (200 ml). The aqueous solution was extracted with EtOAc (3×75 ml). The organic extracts were washed with water (50 ml), dried (MgSO4) and concentrated in vacuo. The crude material was purified on silica gel dry column using first a mixture of CH2Cl2 :EtOAc (1:4) and then EtOAc:Et3N (49:1). Appropriate fractions were concentrated in vacuo leaving yellow crystals, 0.815 g, m.p. 119° C., 64%. 1H NMR (DMSO-d6) δ (ppm): 11.17, 11.11, 10.80 and 10.51 (4 br s, 2H indolic NH, and 5-NH), 7.4 (br s, 1H), 7.26 (s, 1H), 7.07 (d, J=8.2 Hz, 1H), 4.40 (t, J=5.2 Hz, 1H, OH), 3.46 (t, J=3.5 Hz, 2H after D2O exchange), 2.95-3.10 (m, 2H, CH2CH2CH2O), 2.66 (br s, 2H, CH3CH 2 S), 2.26 (br s, 1H, CH3 on dioxocyclobutene), 1.7-1.9 (m, 2H, CH2CH2CH2O), 1.59 (br s, 2H, CH3 on dioxocyclobutene), 0.9-1.1 (m, 3H, CH3CH2S). IR (KBr) n:3420, 3300-3000, 1775, 1728, 1620, 1580 and 1400 cm-1. Anal. calcd. for: C18H20N2O3S: C 62.77; H 5.85; N 8.13; S 9.31. Found: C 62.75; H 5.85; N 8.20; S 9.25.

1. extractionThe aqueous solution was extracted with EtOAc (3×75 ml)
2. washThe organic extracts were washed with water (50 ml)
3. dry with materialdried (MgSO4)
4. concentrationconcentrated in vacuo
5. customThe crude material was purified on silica gel
6. customdry column
7. additiona mixture of CH2Cl2 :EtOAc (1:4)
8. concentrationAppropriate fractions were concentrated in vacuo
9. customleaving yellow crystals, 0.815 g, m.p. 119° C., 64%