Hexachloroethane → 5-chloro-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide

Under a nitrogen atmosphere, N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide (4.0 g, 16 mmol) (i.e. the product of Example 13, Step A) in tetrahydrofuran (25 mL) was cooled to −78° C. was then treated with n-butyllithium (2 M solution in cyclohexane, 8.6 mL, 17.2 mmol) dropwise. The reaction mixture formed a thick precipitate, and stirring was continued for 30 minutes after the addition. To the stirred suspension, a solution of hexachloroethane (4.2 g, 18 mmol) in tetrahydrofuran (15 mL) was added dropwise. After 1 h the resulting clear solution was warmed to ambient temperature and quenched with the addition of water (50 mL). The reaction mixture was extracted with dichloromethane and dried over MgSO4. The reaction mixture was filtered and concentrated under reduced pressure to give 4.38 g of the title compound. This compound was of sufficient purity to use in subsequent reactions.

1. customThe reaction mixture formed a thick precipitate
2. additionafter the addition
3. customquenched with the addition of water (50 mL)
4. extractionThe reaction mixture was extracted with dichloromethane
5. dry with materialdried over MgSO4
6. filtrationThe reaction mixture was filtered
7. concentrationconcentrated under reduced pressure

ORD record

ord-228295c83b0949f299b9255744f217ee

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586611B2