Dimethylformamide → HCID 19007113, compound

To 14.2 g of 8-chloro-5-quinolinesulfonic acid were added 142 ml of thionyl chloride and 1.42 ml of dimethylformamide. The resultant mixture was heated under reflux for 3 hours and the thionyl chloride was removed by distillation under reduced pressure to obtain a residue. The thus obtained residue was dissolved in 100 ml of ice water and adjusted to pH 6 with a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with 100 ml of dichloromethane. The dichloromethane layer was added dropwise to 100 ml of a dichloromethane solution containing 3.56 g of ethanolamine and 5.6 g of triethylamine over 30 minutes while cooling with ice. The mixture was stirred at a temperature of 15° C. to 20° C. for 2 hours. After completion of the reaction, the resultant mixture was washed with 200 ml of water and dried over anhydrous magnesium sulfate. Then, the solvent was removed by distillation under reduced pressure, to thereby obtain 14.0 g of N-(2-hydroxyethyl)-8-chloro-5-quinolinesulfonamide (yield: 84%).

1. temperatureunder reflux for 3 hours
2. customthe thionyl chloride was removed by distillation under reduced pressure
3. customto obtain a residue
4. extractionfollowed by extraction with 100 ml of dichloromethane
5. additionThe dichloromethane layer was added dropwise to 100 ml of a dichloromethane solution
6. additioncontaining 3.56 g of ethanolamine and 5.6 g of triethylamine over 30 minutes
7. temperaturewhile cooling with ice
8. customAfter completion of the reaction
9. washthe resultant mixture was washed with 200 ml of water
10. dry with materialdried over anhydrous magnesium sulfate
11. customThen, the solvent was removed by distillation under reduced pressure

ORD record

ord-d71670c61c1e40ada9e62e22225340b0

Source dataset

uspto-grants-1994_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05340811