反应详情

温度

20 °C

To a solution of sulfamoyl chloride (13.8 g, 0.12 mole) in anhydrous methylene chloride (75 ml) is added a solution of 3-iodo-5-(1,1-dimethylethyl)salicylaldehyde (6 g., 0.02 mole) and triethylamine (12.1 g, 0.12 mole) in anhydrous methylene chloride (100 ml.) dropwise with stirring at 20° C. Upon completing the addition, the resulting reaction mixture is stirred at 20° C. for 3 days. Removal of the solvent in vacuo leaves a tacky residue which is partitioned between ether and 2 N hydrochloric acid. After separating the phases, the organic phase is washed with water and saturated brime, dried over sodium sulfate and filtered. Evaporation of the filtrate leaves an oily residue (6 g.) which is chromatographed on silica gel (300 g.) with benzene. Elution with benzene (840 ml.) gives recovered 3-iodo-5-(1,1-dimethylethyl)salicylaldehyde (2.2 g., 37% recovery), m.p. 76°-78° C. Continued elution with benzene (500 ml.) provides an impure solid (2.4 g.) which is triturated with hexane (20 ml.) and filtered to afford the title compound as a pale yellow solid (1.0 g, 14%), m.p. 130°-134° C. Crystallization from hexane benzene (9.1; viv) gives an analytical sample of 2,2-dioxo-6-(1,1-dimethylethyl)-8-iodo-1,2,3-benzoxathiazine, m.p. 135°-136° C.

1. additionthe addition
2. customthe resulting reaction mixture
3. stirringis stirred at 20° C. for 3 days
4. customRemoval of the solvent in vacuo
5. customleaves a tacky residue which
6. customis partitioned between ether and 2 N hydrochloric acid
7. customAfter separating the phases
8. washthe organic phase is washed with water and saturated brime
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. customEvaporation of the filtrate
12. customleaves an oily residue (6 g.) which
13. customis chromatographed on silica gel (300 g.) with benzene
14. washElution with benzene (840 ml.)
15. customgives
16. customrecovered 3-iodo-5-(1,1-dimethylethyl)salicylaldehyde (2.2 g., 37% recovery), m.p. 76°-78° C
17. washContinued elution with benzene (500 ml.)
18. customprovides an impure solid (2.4 g.) which
19. customis triturated with hexane (20 ml.)
20. filtrationfiltered