反应详情

N-(2,4-dimethoxybenzyl)-1,3-thiazol-2-amine (3.83 g, 0.0153 mol; Icagen) was dissolved in THF (70 mL, 0.8 mol) and cooled in an ice bath. 1.0 M of Lithium hexamethyldisilazide in THF (33 mL) was added dropwise to the reaction. After 30 minutes, a solution of 4-(chlorosulfonyl)benzoic acid (3.07 g, 0.0139 mol) in THF (30 mL, 0.4 mol) was added dropwise to the reaction. The reaction was stirred overnight then quenched with 0.5 N HCl and diluted with ethyl acetate. The phases were separated and the organic phase was washed with 2× with 0.5N HCl. The organic phase was dried over magnesium sulfate, treated with activated carbon and filtered through Celite. The filtrate was evaporated to a residue and triturated with ethyl acetate. The solid was collected by filtration. Vacuum drying afforded the product as a tan solid (2.55 g, 40%).

1. temperaturecooled in an ice bath
2. customthen quenched with 0.5 N HCl
3. additiondiluted with ethyl acetate
4. customThe phases were separated
5. washthe organic phase was washed with 2× with 0.5N HCl
6. dry with materialThe organic phase was dried over magnesium sulfate
7. additiontreated with activated carbon
8. filtrationfiltered through Celite
9. customThe filtrate was evaporated to a residue
10. customtriturated with ethyl acetate
11. filtrationThe solid was collected by filtration
12. customVacuum drying