反应详情

To a solution of 5-iodoanthranilic acid methyl ester (1.00 g) and triethylamine (1.01 mL) in CH2Cl2 (25 mL) is added methanesulfonyl chloride (0.59 mL) at 0° C. The ice bath is removed and after 3 h at room temperature the solution is poured into water (20 mL) and extracted with CH2Cl2 (2×20 mL). The organic layers are combined, dried over MgSO4 and the solvent removed in vacuo. The resulting residue is dissolved in CH3OH (20 mL) and sodium methoxide (20 mL) is added. After 45 min, the solvent is removed in vacuo. The residue is diluted with Et2O (20 mL) and washed with water (20 mL). The organic layer is separated, dried over MgSO4, filtered, and concentrated in vacuo. The crude black liquid is purified by silica gel column chromatography (4/1, hexanes/EtOAc ) to afford 0.58g (46%) of the title compound as a brown solid. Physical characteristics: m.p. 119-120° C.; 1H NMR (300 MHz, CDCl3) δ 10.41, 8.36, 7.82, 7.52, 3.94, 3.06; IR (diffuse reflectance) 1700, 1682, 1483, 1385, 1335, 1328, 1307, 1249, 1213, 1159, 1147, 1093, 1086, 978, 971 cm−1; MS (FAB) m/z 356 (MH+); HRMS (FAB) m/z 355.9447 (C9H10INO4S+H). Anal. Found: C, 30.49; H, 2.88; N, 3.96.

1. customThe ice bath is removed and after 3 h at room temperature the solution
2. additionis poured into water (20 mL)
3. extractionextracted with CH2Cl2 (2×20 mL)
4. dry with materialdried over MgSO4
5. customthe solvent removed in vacuo
6. dissolutionThe resulting residue is dissolved in CH3OH (20 mL)
7. additionsodium methoxide (20 mL) is added
8. customthe solvent is removed in vacuo
9. additionThe residue is diluted with Et2O (20 mL)
10. washwashed with water (20 mL)
11. customThe organic layer is separated
12. dry with materialdried over MgSO4
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. customThe crude black liquid is purified by silica gel column chromatography (4/1, hexanes/EtOAc )