Ammonium Chloride → 3,N-Dimethoxy-N-methyl-5-(pentafluorosulfanyl)benzamide

Temperature

-15 °C

Methyl 3-methoxy-5-(pentafluorosulfanyl)benzoate (81 mg) was dissolved in absolute THF (5 ml), and N,O-dimethylhydroxylamine hydrochloride (42 mg) was added. Then the mixture was cooled to −15° C., and isopropylmagnesium bromide solution (0.21 ml, 2 M in THF) was added dropwise. After 20 min, the cooling bath was removed and the mixture was stirred at RT for 1 h. To complete the reaction, the mixture was twice more cooled to −15° C., isopropylmagnesium bromide solution (0.1 ml each time) was added dropwise and the mixture was stirred at RT for 1 h. Then ammonium chloride solution was added (10 ml) and the aqueous phase was extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 70 mg of the desired compound were obtained.

1. customthe cooling bath was removed
2. customthe reaction
3. temperaturethe mixture was twice more cooled to −15° C.
4. stirringthe mixture was stirred at RT for 1 h
5. extractionthe aqueous phase was extracted three times with ethyl acetate
6. dry with materialThe combined extracts were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-c07555d942ab4cc6be5a3e08622d9cd8

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466169B2