Dimethylcarbamoyl Chloride → 6-Methylpyridine-2-carbonitrile

2-Methyl-pyridine 1-oxide (10.9 g, 100 mmol) was dissolved into methylene chloride (100 mL) and dried over MgSO4. The solution was filtered and the filtrate was added to trimethylsilyl cyanide (16.7 mL, 125 mmol) at ambient temperature. To which was added dropwise a solution of dimethylcarbamyl chloride (11.5 mL, 125 mmol) in methylene chloride (25 mL). The resulting mixture was stirred at ambient temperature for 24 h. A solution of 10% K2CO3 was added slowly to the reaction mixture and stirring was continued for 10 minutes after the addition was complete. The layers were separated and the aqueous layer was extracted with methylene chloride (2×50 mL). The combined organic extracts were dried (Na2SO4), and concentrated to dryness under high vacuum to yield the title compound I-4h (6.64 g).

1. dry with materialdried over MgSO4
2. filtrationThe solution was filtered
3. stirringstirring
4. waitwas continued for 10 minutes
5. additionafter the addition
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with methylene chloride (2×50 mL)
8. dry with materialThe combined organic extracts were dried (Na2SO4)
9. concentrationconcentrated to dryness under high vacuum

ORD record

ord-1bb95ea648d146b19146726eee4d9028

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06894050B2