Hexachloroethane → HCID 59589496, compound

Under a nitrogen atmosphere, a solution of N,N-dimethyl-1H-pyrazole-1-sulfonamide (5.0 g, 28 mmol) (i.e. the product of Example 12, Step A) in tetrahydrofuran (50 mL) was cooled to −78° C. and then treated with n-butyllithium (2 M solution in cyclohexane, 15.0 mL, 30 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 (7.1 g, 30 mmol) in tetrahydrofuran (20 mL) was added dropwise. After 30 minutes the resulting clear solution was warmed to ambient temperature and quenched with the addition of water (70 mL). The reaction mixture was extracted with dichloromethane and dried over MgSO4. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (50% hexanes in dichloromethane as eluant) to give 1.71 g of 5-chloro-N,N-dimethyl-1H-pyrazole-1-sulfonamide. The 5-chloro-N,N-dimethyl-1H-pyrazole-1-sulfonamide was heated to 110° C. for 12 h with a catalytic amount of pyrazole to isomerize to the title compound.

1. customThe reaction mixture formed a thick precipitate
2. additionafter the addition
3. customquenched with the addition of water (70 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
8. customThe crude product was purified by silica gel chromatography (50% hexanes in dichloromethane as eluant)

ORD record

ord-80b7f09409c74758aa9854fd1d6b2354

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586611B2