Formaldehyde → 5-Chloro-3-(1H-imidazol-1-yl)-1,2,4-thiadiazole

Temperature

80 °C

5-Chloro-[1,2,4]thiadiazol-3-ylamine (1.00 g, 7.40 mmol) and glyoxal 40% wt (5.35 g, 92.0 mmol) were dissolved in ethanol (100 mL). The solution was stirred at 80° C. for 4 hours. Ammonium chloride (1.97 g, 37.0 mmol), formaldehyde (2.97 g, 37.0 mmol) and phosphoric acid (2.97 g, 30.0 mmol) were added to the solution and stirred overnight. The reaction was concentrated down under vacuo and redissolved in water (50 mL). The solution was extracted with ethyl acetate (2×50 mL). The aqueous layer was neutralized with 1M NaOH, extracted with ethyl acetate (2×50 mL), dried over MgSO4 and concentrated under vacuo to afford 200 mg (20%) of 5-chloro-3-imidazol-1-yl-[1,2,4]thiadiazole. 1H-NMR (400 MHz, CDCl3) δ 8.84 (s, 1H), 7.75 (d, 1H), 7.22 (d, 1H).

1. stirringstirred overnight
2. concentrationThe reaction was concentrated down under vacuo
3. dissolutionredissolved in water (50 mL)
4. extractionThe solution was extracted with ethyl acetate (2×50 mL)
5. extractionextracted with ethyl acetate (2×50 mL)
6. dry with materialdried over MgSO4
7. concentrationconcentrated under vacuo

ORD record

ord-ee080a224b1f4fd09566b423ba8287fc

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07825256B2