Dimethylcarbamoyl Chloride → HCID 66718549, compound

Temperature

40 °C

(S)-2-(Tetrahydrofuran-3-yloxymethyl)pyridine-1-oxide (24.08 g, 0.123 mol, 1 eq) was dissolved in anhydrous DCM (400 mL). N,N-Dimethylcarbamyl chloride (19.89 g, 0.185 mol, 1.5 eq) was added followed by trimethylsilyl cyanide (18.35 g, 0.185 mol, 1.5 eq). The solution was stirred at 40° C. for 24 hours (solution had turned red). The reaction was cooled to room temperature, then 2 M aqueous Na2CO3 solution was added (80 mL) and stirred overnight. The emulsion was filtered off, leaving the white precipitate behind. The layers were separated and the organic layer was evaporated to leave a brown oil. This was dissolved in ethyl acetate (160 mL), 2-M aqueous Na2CO3 solution (160 mL) was added and stirred for 2 hours. The layers were separated and the organic layer was washed with saturated brine (30 mL), dried over Na2SO4 and evaporated to a brown oil; LC-MS Retention time 1.82 min; (M+H)+ 205.

1. temperatureThe reaction was cooled to room temperature
2. stirringstirred overnight
3. filtrationThe emulsion was filtered off
4. customleaving the white precipitate behind
5. customThe layers were separated
6. customthe organic layer was evaporated
7. customto leave a brown oil
8. stirringstirred for 2 hours
9. customThe layers were separated
10. washthe organic layer was washed with saturated brine (30 mL)
11. dry with materialdried over Na2SO4
12. customevaporated to a brown oil

ORD record

ord-58fa351b49c347459872a9804ebb90d0

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450328B2