Hydrochloric Acid → HCID 10332165, compound

Into a solution of 3-cyano-5-isopropylaminopyridine (118 mg, 0.73 mmol) in 1-propanol (20 ml) was passed hydrogen chloride gas under ice-cooling for 30 minutes. The reactor was tight sealed, and the mixture was stirred at room temperature for 17 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure, and the residue was neutralized with a saturated sodium carbonate solution and extracted with chloroform (50 ml×3). The chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a yellow syrup. To the syrup was then added an aqueous solution (6 ml) of cyanamide (61 mg, 1.45 mmol), Na2HPO4 (104 mg, 0.73 mmol) and NaH2PO4 ·2H2O (456 mg, 2.92 mmol), and the mixture was stirred at room temperature for 22 hours. After the reaction was completed, the reaction mixture was extracted with chloroform (30 ml×3), and the chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give propyl N-cyano-5-isopropylamino-3-pyridinecarboximidate (80 mg, 0.33 mmol) as a yellow syrup (Yield 44%).

1. temperaturecooling for 30 minutes
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. extractionextracted with chloroform (50 ml×3)
4. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customto give a yellow syrup
7. stirringthe mixture was stirred at room temperature for 22 hours
8. extractionthe reaction mixture was extracted with chloroform (30 ml×3)
9. dry with materialthe chloroform layer was dried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-ea26c595f5764c1bb942f600affb55e8

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05508293