Hexane → HCID 19882353, compound

A solution of S-methyl-S-(thien-3-yl)sulfoximine (Maybridge, 2.56 g, 15.9 mmol) in dimethylformamide (15 mL) was added dropwise to a slurry of sodium hydride (0.76 g, 19.0 mmol, 60% oil dispersion, washed (3×8 mL) hexane) in dimethylformamide (10 mL) at 0° C. The solution was allowed to warm to ambient temperature and was stirred at ambient temperature for 0.5 h. The resulting mixture was cooled to 0° C. and a solution of 1-chloro-2-diethylaminoethane (2.14 g, 15.9 mmol) in dimethylformamide (15 mL) was added dropwise. The reaction mixture was stirred at ambient temperature for 15 h. Water (1 mL) was added and the reaction mixture was concentrated in vacuo. The residue was partitioned between water (25 mL) and methylene chloride (25 mL). The layers were separated and the aqueous layer was extracted with methylene chloride (2×25 mL). The combined organic extracts were washed (saturated sodium chloride), dried (MgSO4), and concentrated in vacuo to afford 3.9 g of residue. The residue was chromatographed (flash, SiO2, 9:1:0 to 9:1:1 methylene chloride/methanol/concentrated ammonium hydroxide) to give an oil that was partitioned between water (15 mL) and methylene chloride (15 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The oil partially solidified on standing.

1. temperatureThe resulting mixture was cooled to 0° C.
2. stirringThe reaction mixture was stirred at ambient temperature for 15 h
3. concentrationthe reaction mixture was concentrated in vacuo
4. customThe residue was partitioned between water (25 mL) and methylene chloride (25 mL)
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with methylene chloride (2×25 mL)
7. washThe combined organic extracts were washed (saturated sodium chloride)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo

ORD record

ord-78e95ddffb6946f39c3dcb802e313f33

Source dataset

uspto-grants-1992_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05140026