Methanamine, N-methoxy-, hydrochloride (1:1) → 3,N-Dimethoxy-N-methyl-5-(pentafluorosulfanyl)benzamide

Temperature

-15 °C

Methyl 3-methoxy-5-(pentafluorosulfanyl)benzoate (O4.007; 2.5 g) was dissolved in absolute THF (65 ml), and N,O-dimethylhydroxylamine hydrochloride (1.2 g) was added. Then the mixture was cooled to −15° C. and isopropylmagnesium bromide solution (13.59 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. Then ammonium chloride solution was added and the aqueous phase was extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The crude product thus obtained still contained significant reactant, and was therefore converted and worked up again as described above. No reactant was present any longer in the residue which was then obtained. Purification was effected by means of preparative HPLC (met. A). The product-containing fractions were combined and freed of the acetonitrile, and the aqueous phase was extracted three times with EA. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 1.78 g of the desired compound were obtained.

1. customthe cooling bath was removed
2. additionThen ammonium chloride solution was added
3. extractionthe aqueous phase was extracted three times with ethyl acetate
4. dry with materialThe combined extracts were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude product thus obtained still contained significant reactant
8. customwas then obtained
9. customPurification
10. extractionthe aqueous phase was extracted three times with EA
11. dry with materialThe combined extracts were dried over magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-058e8ca8eb854d3c9f583e52149a51c1

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076336B2