Sodium borohydride → N-(2-chloro-5-pyridylmethyl)2-aminoethanethiol

A solution composed of 6-chloronicotinaldehyde (14.2 g), 2-aminoethanethiol (7.7 g) and benzene (80 ml) was heated with stirring for 5 hours while removing water as an azeotrope. After the reaction, benzene was distilled off under reduced pressure, and further volatile materials were removed at 1 mmHg and 70° C. to give 2-(2-chloro-5-pyridyl)thiazolidine (18 g) as a residue. Ten grams of 2-(2-chloro-5-pyridyl)thiazolidine was dissolved in 100 ml of ethanol, and sodium borohydride was added. With stirring, the mixture was gradually heated and thereafter re-fluxed for 1 hour. Ethanol was distilled off under reduced pressure, and chloroform was added to the residue. Insoluble materials were separated by filtration and the chloroform layer was washed with water and dehydrated. Chloroform was distilled off under reduced pressure to give the desired N-(2-chloro-5-pyridylmethyl)2-aminoethanethiol (8.3 g).

1. temperaturethe mixture was gradually heated
2. distillationEthanol was distilled off under reduced pressure, and chloroform
3. additionwas added to the residue
4. customInsoluble materials were separated by filtration
5. washthe chloroform layer was washed with water
6. distillationChloroform was distilled off under reduced pressure

ORD record

ord-1f4a32913f604435acfd8bd1c5b7a5c6

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06022967