Acetic Acid → HCID 63386443, compound

Temperature

23 °C

To a mixture of 5-pyridin-3-yl-[1,3,4]thiadiazol-2-ylamine (5.5 g, 30.9 mmol) and copper powder (0.335 g, 5.27 mmol), in a mixture of glacial acetic acid (93 mL) and concentrated hydrochloric acid (19 mL) at 0° C., was added dropwise a solution of sodium nitrite (10.67 g, 154.6 mmol) dissolved in water (13 mL). The reaction mixture was then allowed to warm to 23° C. overnight. The reaction mixture was diluted with 300 g of ice, resulting in an emulsion, and extracted with dichloromethane (3×200 mL). The emulsion was then passed through a medium porosity scintered glass funnel containing celite. The cake was stirred and washed well with chloroform. The filtrate was combined with the organic extracts. The organic phase was dried over MgSO4 and concentrated to dryness to give the title compound as a yellow solid (4.42 g, 72%): 1H NMR (300 MHz, CDCl3) δ 9.08 (br s, 1H), 8.78 (br s, 1H), 8.29 (dt, J=8, 2 Hz, 1H), 7.49 (dd, J=8, 5 Hz, 1H).

1. customresulting in an emulsion
2. extractionextracted with dichloromethane (3×200 mL)
3. additioncontaining celite
4. washwashed well with chloroform
5. dry with materialThe organic phase was dried over MgSO4
6. concentrationconcentrated to dryness

ORD record

ord-e719b91fe9e648d6805b5ace44998856

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604211B2