2-Mercaptoethanol → HCID 18433349, compound

Under a nitrogen atmosphere, a mixture of 2-mercaptoethanol (3.30 g, 42.21 mmol), sodium hydroxide (1.69 g, 42.21 mmol) and N,N-dimethylformamide (50 mL) was stirred at ambient temperature for 4 h. The resulting solution was cooled to 0-5° C. and 3,5-dibromopyridine (8.00 g, 33.77 mmol) was added in one portion. The mixture was stirred at 0-5° C. for 20 min, warmed to ambient temperature and further stirred for 1 h. TLC analysis on silica gel eluting with EtOAc-hexane (3:1) indicated an incomplete reaction. Therefore, the mixture was heated at 75° C. (oil bath temperature) for 1 7 h. After cooling to ambient temperature, the mixture was poured into water (250 mL) and extracted with ether (3×75 mL). The combined ether extracts were dried (Na2SO4), filtered and concentrated (rotary evaporator) to a light-yellow oil. The oil was vacuum distilled using a short-path distillation apparatus to afford 4.55 g (57.5%) of a light-yellow oil, bp 138-140° C. at 0.35 mm Hg.

1. temperatureThe resulting solution was cooled to 0-5° C.
2. stirringThe mixture was stirred at 0-5° C. for 20 min
3. temperaturewarmed to ambient temperature
4. stirringfurther stirred for 1 h
5. customan incomplete reaction
6. temperatureTherefore, the mixture was heated at 75° C. (oil bath temperature) for 1 7 h
7. temperatureAfter cooling to ambient temperature
8. extractionextracted with ether (3×75 mL)
9. dry with materialThe combined ether extracts were dried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated
12. custom(rotary evaporator) to a light-yellow oil
13. distillationdistilled

ORD record

ord-03a6a13103324b01a0543c22adb097c6

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1