Hydrochloric Acid → HCID 57500750, compound

To a solution of 3-methyl-6-nitrothiopheno[2,3-d]1,2,3-triazin-4-one (1.25 g, 5.9 mmol) in methanol (50 mL) was added conc. Hydrochloric acid (0.6 mL). To the above solution was added iron powder (1.67 g, 29.5 mmol) followed by a solution of ammonium chloride (1.57 g, 29.5 mmol) in water (10 mL) at rt. The reaction mixture was stirred and warmed to 70 for 1 h and was then allowed to cool to rt. The solution was filtered and basified with saturated sodium bicarbonate solution. The solution was extracted with ethyl acetate (4×100 mL). The combined organic layer was dried over sodium sulfate and filtered. Solvent was evaporated and the residue was chromatographed over silica gel column using hexane-ethyl: acetate (60:40) as eluents to give the product as a pale yellow color solid (80 mg, 7.5%), mp 190-194° C. 1H NMR (400 MHz, DMSO-d6): δ 7.40 (2H, s), 6.11 (1H, s), 3.82 (3H, s); LC-MS (negative ion mode): m/z 181 (M−H)−.

1. temperaturewarmed to 70 for 1 h
2. filtrationThe solution was filtered
3. extractionThe solution was extracted with ethyl acetate (4×100 mL)
4. dry with materialThe combined organic layer was dried over sodium sulfate
5. filtrationfiltered
6. customSolvent was evaporated
7. customthe residue was chromatographed over silica gel column

ORD record

ord-03c51e4e4cf3494793c65fa351d44ece

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258119B2