Dimethylformamide → HCID 21699006, compound

Temperature

17.5 °C

In accordance with the process disclosed in Aust. J. Chem. 40, 1179 (1987), the mixture of 2-fluoro-4-methoxyacetophenone (3 g, 22.73 mmol), N,N-dimethylformamide (25 ml), benzene (17.5 ml) and carbon disulfide (3.78 g, 50.01 mmol) was stirred and added with 55% sodium hydride (2.42 g, 55.47 mmol) over about 2.5 hours while inner temperature was maintained at 15-20° C. After additional stirring for 30 minutes, the reaction mixture was added with methanol (0.5 ml) and further stirred for 15 minutes. Benzene was removed under heating to increase inner temperature up to 125-130° C.; at that temperature range, the mixture was heated for 45 minutes and was allowed to cool to room temperature. The reaction mixture was added with water (80 ml) and acetic acid (2.5 ml) and extracted with ether (50 ml×2 times); water layer was filtered out and acidified with concentrated hydrochloric acid. The resulting precipitates were collected by filteration and were recrystallized from methanol-1,2-dichloroethane (1:1) to obtain 3.8 g (yield: 75%) of the titled compound.

1. stirringAfter additional stirring for 30 minutes
2. stirringfurther stirred for 15 minutes
3. customBenzene was removed
4. temperatureunder heating
5. temperatureto increase inner temperature up to 125-130° C.
6. temperatureat that temperature range, the mixture was heated for 45 minutes
7. temperatureto cool to room temperature
8. additionThe reaction mixture was added with water (80 ml) and acetic acid (2.5 ml)
9. extractionextracted with ether (50 ml×2 times)
10. filtrationwater layer was filtered out
11. customThe resulting precipitates
12. customwere collected by filteration
13. customwere recrystallized from methanol-1,2-dichloroethane (1:1)

ORD record

ord-7ef50943bd1f4260a52233529118c222

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06294527B1