Sodium Nitrite → HCID 136155074, compound

Temperature

0 °C

To an ice cold (0° C.) solution of 3-aminobenzo[b]selenophene-2-carboxamide (1.0 g, 4.16 mmol) in concentrated sulfuric acid (25 mL) was added a cold (0° C.) solution of sodium nitrite (0.316 g, 4.58 mmol) in concentrated sulfuric acid (10 mL) for 10 min (while adding, the temperature should keep between −5-0° C.). After addition, the mixture was stirred at 0° C. for 1 h and at rt for 2 h. The reaction mixture was cooled, poured into crushed ice slowly with stirring for 15 min and stirred at the same temperature for 15 min. The solution was extracted with ethyl acetate (3×200 mL) and the combined EtOAc layer was washed with water, brine and dried over sodium sulfate. The solution was filtered, evaporated the solvent to give the product as a yellow color solid (200 mg, 19%), mp 176-178° C. 1H NMR (400 MHz, DMSO-d6): δ 15.48 (1H, s, —NH), 8.53-8.58 (1H, m, H-9), 8.41-8.46 (1H, m, H-6), 7.74-7.80 (2H, m, H-7,8).

1. additionwhile adding
2. customshould keep between −5-0° C.
3. additionAfter addition
4. temperatureThe reaction mixture was cooled
5. additionpoured
6. custominto crushed ice slowly
7. stirringwith stirring for 15 min
8. stirringstirred at the same temperature for 15 min
9. extractionThe solution was extracted with ethyl acetate (3×200 mL)
10. washthe combined EtOAc layer was washed with water, brine
11. dry with materialdried over sodium sulfate
12. filtrationThe solution was filtered
13. customevaporated the solvent

ORD record

ord-0f3fc94c0fe44555a3df34c2862cd2c3

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143237B2