反应详情

Methyl 2-(chlorosulfonyl)benzoate (14.1 g, 60.0 mmol) was added to a stirred solution of 3-pyridinamine (15.0 g, 159.4 mmol) in CH3CN (0.4 M). The temperature rose to 25° C. and a small amount of reddish oil separated out. CHCl3 (2.0 M, protected with amylenes) was added to return all materials to solution. After 1 h, the solvents were evaporated and the residual oil was partitioned between EtOAc and water. The organic layer was washed with water and was evaporated to give the crude product. The crude product was dissolved in the minimum amount of hot EtOAc and was diluted with ether. The product rapidly crystallized out and after 1 hour filtered off and washed with ether to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 8.38 (d, 1H) 8.31 (d, 2H) 7.93 (d, 2H) 7.80 (d, 2H) 7.76 (t, 1H) 7.64 (t, 1H) 7.53 (t, 1H) 7.25 (m, 1H) 4.12 (s, 3H).

1. customrose to 25° C.
2. customa small amount of reddish oil separated out
3. additionCHCl3 (2.0 M, protected with amylenes) was added
4. customthe solvents were evaporated
5. customthe residual oil was partitioned between EtOAc and water
6. washThe organic layer was washed with water
7. customwas evaporated
8. customto give the crude product
9. customThe product rapidly crystallized out and after 1 hour
10. filtrationfiltered off
11. washwashed with ether