反应详情

温度

110 °C

By the method of Feutrill, G. I.; Mirrington, R. N. Tet. Lett. 1970, 1327; the aryl methyl ether is converted to the phenol derivative. To 2-anilino-6-methoxy-quinoxaline (0.27 g, 1.07 mmol) under argon in DMF is added the sodium salt of ethanethiol (0.19 g, 2 mmol). The reaction mixture is heated to 110° C. overnight. The mixture is concentrated and partitioned between EtOAc and H2O/5% tartaric acid such that the pH of the aqueous layer is approximately 4. The organic layer is washed with 120 (4X), then with 2.5% NaOH (4X). The basic layers combined, washed with EtOAc (2X), re-acidified with 5% tartaric acid, and washed with multiple portions of EtOAc. The organic layers are combined, washed with brine, dried (Na2SO4), and concentrated. The resulting solid is chromatographed (50% EtOAc/hexanes). An analytical sample is obtained by triturating the product with Et2O to provide a yellow powder (m.p. 211-213° C.). Anal. Calcd. for C14H11N3O: C, 70.88; H, 4.67: N, 17.71; Found: C, 70.64; H, 4.85; N, 17.58.

1. concentrationThe mixture is concentrated
2. custompartitioned between EtOAc and H2O/5% tartaric acid such that the pH of the aqueous layer
3. washThe organic layer is washed with 120 (4X)
4. washwashed with EtOAc (2X), re-acidified with 5% tartaric acid
5. washwashed with multiple portions of EtOAc
6. washwashed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. customThe resulting solid is chromatographed (50% EtOAc/hexanes)
10. customAn analytical sample is obtained
11. customby triturating the product with Et2O