Water → HCID 18185381, compound

To 10 g (63.47 mmol) 2-chloropyridine-5-carboxylic acid were added 60 g (507 mmol) thionylchloride and the mixture was refluxed for 3 h. Excess thionylchloride was distilled off, ether (50 ml) was added and evaporated to remove traces of thionylchloride. The residue was dissolved in 30 ml dichloromethane and added dropwise to a solution of 11.88 g (0.133 mmol) 2-amino-2-methylpropanol in 30 ml dichloromethane at 0° C. The reaction mixture was stirred for 2 hours at room temperature and 30 ml water were added. The layers were separated and the aqueous phase was extracted again with dichloromethane. The combined organic layers were dried with magnesium sulfate and evaporated to yield an oily liquid. To the residue were added 22.6 g (190 mmol) of thionylchloride at 0° C. and the mixture was stirred for 30 min. Ethyl acetate was added, the mixture was stirred for another 30 min and the crystals were washed with ethyl acetate and ether to yield 14 g (89%) of a white solid.

1. temperaturethe mixture was refluxed for 3 h
2. distillationExcess thionylchloride was distilled off
3. additionether (50 ml) was added
4. customevaporated
5. customto remove traces of thionylchloride
6. dissolutionThe residue was dissolved in 30 ml dichloromethane
7. customThe layers were separated
8. extractionthe aqueous phase was extracted again with dichloromethane
9. dry with materialThe combined organic layers were dried with magnesium sulfate
10. customevaporated
11. customto yield an oily liquid
12. stirringthe mixture was stirred for 30 min
13. stirringthe mixture was stirred for another 30 min
14. washthe crystals were washed with ethyl acetate and ether

ORD record

ord-6a93c65bfcb542ccb823945a467f5850

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06596773B2