Sodium methanethiolate → 3-Pyridinecarboxamide, 5-mercapto-N,N-dimethyl-

Temperature

100 °C

Sodium thiomethoxide (3 g) was added to a stirred solution of 5-bromo-N,N-dimethyl-3-pyridinecarboxamide (2.5g, WO2000055168) in N,N-dimethylformamide (40 ml) and the suspension stirred at 100° C. for 4 h. The solvent was concentrated in vacuo, the residue dissolved in 2M sodium hydroxide (35 ml) and water (50 ml), and the solution washed with chloroform (4×75 ml). The aqueous layer was acidified with 2M hydrochloric acid to pH 4 and extracted with chloroform (5×80 ml), and the combined organic layers were washed with brine (20 ml), dried over magnesium sulphate and concentrated in vacuo to give the title compound as an orange oil (1.8 g).

1. concentrationThe solvent was concentrated in vacuo
2. dissolutionthe residue dissolved in 2M sodium hydroxide (35 ml)
3. washwater (50 ml), and the solution washed with chloroform (4×75 ml)
4. extractionextracted with chloroform (5×80 ml)
5. washthe combined organic layers were washed with brine (20 ml)
6. dry with materialdried over magnesium sulphate
7. concentrationconcentrated in vacuo

ORD record

ord-a57ceb05a5074d88afd100135ff47684

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07566786B2