Hydrochloric Acid → HCID 121268896, compound

Temperature

100 °C

To a solution of 3-iodo-5-isocyanopyridine (2.4 g, 10.43 mmol, 1 eq) in anhydrous DMF (25 mL) in a round bottom flask was added ammonium chloride (0.95 g, 1.7 eq) and sodium azide (1.15 g, 1.7 eq). After the reaction mixture was heated and stirred at 100° C. under anhydrous nitrogen atmosphere for 16 hours, it was cooled to room temperature and poured into ice water. 2 N HCl was dropwise added to adjust the pH ˜3 followed by a further stirring for about 30 minutes. The aqueous layer was first extracted with ethyl acetate, followed by an extraction with THF-EtOAc (1:9), and lastly an extraction with i-PrOH—CHCl3 (1:6). All organic solvents were combined and dried with anhydrous sodium sulfate. The upper clear liquor was decanted, concentrated, and the resulting solid residue was treated with EtOAc-Hex (1:9). After the mixture was stirred about 16 hours, it was filtered to yield 3-iodo-5-(2H-tetrazol-5-yl)pyridine as white solid in the amount of 2.36 g.

1. temperatureAfter the reaction mixture was heated
2. temperatureit was cooled to room temperature
3. stirringa further stirring for about 30 minutes
4. extractionThe aqueous layer was first extracted with ethyl acetate
5. extractionfollowed by an extraction with THF-EtOAc (1:9)
6. extractionlastly an extraction with i-PrOH—CHCl3 (1:6)
7. dry with materialdried with anhydrous sodium sulfate
8. customThe upper clear liquor was decanted
9. concentrationconcentrated
10. additionthe resulting solid residue was treated with EtOAc-Hex (1:9)
11. stirringAfter the mixture was stirred about 16 hours
12. filtrationit was filtered

ORD record

ord-1f1ae9689faa4d8183481614407259b6

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359336B2