反应详情

A solution of 3.0 g (0.001 mol) of α-acetyl-N,N-di-methyl-3-nitrostyrenesulfonamide and 1.43 g (0.01 mol) of 3-aminocrotonic acid isopropyl ester in 30 ml of isopropanol is heated to reflux for 2 hours thereupon treated with 1.16 q (0.005 mol) of DL-camphor-10-sulfonic acid and then heated to reflux for an additional 15 minutes. After concentration under reduced pressure, the oily residue is partitioned between water and methylene chloride the organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated graphed on 350 g of silica gel with methylene chloride/ethyl acetate (9:1) as the elution agent. The homogeneous fractions yield an oil which crystallizes upon trituration with ether. After recrystallization from methylene chloride/ether, there are obtained 3.2 g (75.5%) of 5-(di-methylsulfamoyl)-1.4-dihydro-2,6 -dimethyl-4-(3-nitrophenyl)-nicotinic acid isopropyl ester, m.p. 136°-138°, as a yelloWish crystalline powder.

1. temperatureto reflux for 2 hours
2. temperatureheated
3. temperatureto reflux for an additional 15 minutes
4. concentrationAfter concentration under reduced pressure
5. customthe oily residue is partitioned between water and methylene chloride the organic phase
6. washis washed with a saturated aqueous solution of sodium chloride
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customThe homogeneous fractions yield an oil which
10. customcrystallizes upon trituration with ether
11. customAfter recrystallization from methylene chloride/ether, there