Ammonium Hydroxide → Thieno(2,3-c)pyridine

Temperature

40 °C

The material from Step ii (23.5 g, 61.6 mmol), was dissolved in 100 mL CH2Cl2. The three neck flask was fitted with a reflux condenser and internal thermometer under N2 atmosphere. The flask was evacuated and purged with nitrogen. Titanium (IV) chloride (40 mL, 369 mmol) was added to the reaction slowly. The reaction temperature was maintained at around 40° C. After about 15 mL were added, the reaction was placed in an ice bath to control the temperature. The reaction was allowed to gradually warm to room temperature before heating to 40° C. overnight. The reaction was heated to 40° C. for 18 hours, then cooled to room temperature. The reaction contents were poured, in portions, into a large beaker containing 200 g of ice and 200 mL NH4OH with lots of fuming observed. The reaction was stirred vigorously for a few minutes. The reaction was filtered and the solid was rinsed with CHCl3 (3×100 mL).

1. customThe three neck flask was fitted with a reflux condenser
2. customThe flask was evacuated
3. custompurged with nitrogen
4. additionAfter about 15 mL were added
5. customthe reaction was placed in an ice bath
6. temperatureto gradually warm to room temperature
7. temperaturebefore heating to 40° C. overnight
8. temperatureThe reaction was heated to 40° C. for 18 hours
9. temperaturecooled to room temperature
10. customThe reaction contents
11. additionwere poured, in portions, into a large beaker
12. filtrationThe reaction was filtered
13. washthe solid was rinsed with CHCl3 (3×100 mL)

ORD record

ord-2c8871c194fa42a5accc9483599ff39e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090625B2