Iodoethane → HCID 66743233, compound

Temperature

-78 °C

To a stirred solution of N,N-dimethyl-1H-pyrazole-1-sulfonamide (25.3 g, 144 mmol) in THF (200 mL) at −78° C. was added dropwise 1.6 M n-butyllithium in hexane (99 ml, 159 mmol). After 30 min, iodoethane (12.8 mL, 159 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 30 min and allowed to room temperature slowly. After 1 h, the stirring became difficult by formation of white precipitate. THF (200 mL) was added dropwise to give yellow solution. The stirring was continued for 2 h. Then, the mixture was poured into saturated aqueous NaHCO3 (600 mL) and extracted with EtOAc (400 mL×2), and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to 30:70 hexane/EtOAc) to afford the title compound (19.8 g, 68%) as colorless liquid:

1. customallowed to room temperature
2. waitAfter 1 h
3. customto give yellow solution
4. waitThe stirring was continued for 2 h
5. extractionextracted with EtOAc (400 mL×2)
6. dry with materialthe extract was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by column chromatography (Purif, silica gel, hexane to 30:70 hexane/EtOAc)

ORD record

ord-cb9ca57a20fc4131afcbce8930b76f77

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691828B2