Sodium Chloride → HCID 178512372, compound

Temperature

5 °C

4-Amino methyl pyridine (16.22 g) is added to a stirred suspension of N-cyano-O-(m-cresyl)pseudourea (27.51 g) in 200 ml of isopropanol. The mixture is heated to boiling and refluxed for five hours. The reaction mixture is filtered and the filtrate evaporated under reduced pressure. The residue is stirred in 250 ml of chloroform overnight, the solvent removed under reduced pressure, treated with 250 ml of diethyl ether, the ether decanted and the residual gum treated with 200 ml of 5% HCl and stirred at room temperature for one hour. The mixture is filtered, extracted twice with 200 ml portions of diethyl ether and cooled to about 5° C. The solution is treated carefully with a 50% aqueous sodium hydroxide solution to a pH of 9 and extracted twice with 250 ml portions of methylene chloride. The organic extracts are combined, dried, filtered and evaporated to dryness under reduced pressure leaving a small amount of colored liquid. The aqueous layer is saturated with sodium chloride and re-extracted. After drying, the extracts are evaporated under reduced pressure. The aqueous phase is concentrated under reduced pressure and diluted with ethanol. The precipitated salts are removed by filtration and the filtrate concentrated under reduced pressure. The residue is azeotroped with 150 ml of toluene. The residue is stirred with 250 ml of isopropanol, filtered and evaporated under reduced pressure. The residue is triturated with 250 ml of isopropanol and filtered. The filtrate is dried, filtered, and evaporated under reduced pressure. The residue is taken up in a methanol/ethyl acetate mixture and allowed to stand. After trituration, the mixture is stirred in water overnight, the precipitate then collected and dried in air. The off-white solid is recrystallized from water yielding 12.10 g of pale yellow crystals which are dried in vacuo (55° C.), MP 92°- 93° C. IR and elemental analysis indicate the desired guanidine.

1. temperatureThe mixture is heated
2. temperaturerefluxed for five hours
3. filtrationThe reaction mixture is filtered
4. customthe filtrate evaporated under reduced pressure
5. customthe solvent removed under reduced pressure
6. additiontreated with 250 ml of diethyl ether
7. customthe ether decanted
8. additionthe residual gum treated with 200 ml of 5% HCl
9. stirringstirred at room temperature for one hour
10. filtrationThe mixture is filtered
11. extractionextracted twice with 200 ml portions of diethyl ether
12. additionThe solution is treated carefully with a 50% aqueous sodium hydroxide solution to a pH of 9
13. extractionextracted twice with 250 ml portions of methylene chloride
14. customdried
15. filtrationfiltered
16. customevaporated to dryness under reduced pressure
17. customleaving a small amount of colored liquid
18. extractionre-extracted
19. customAfter drying
20. customthe extracts are evaporated under reduced pressure
21. concentrationThe aqueous phase is concentrated under reduced pressure
22. additiondiluted with ethanol
23. customThe precipitated salts are removed by filtration
24. concentrationthe filtrate concentrated under reduced pressure
25. customThe residue is azeotroped with 150 ml of toluene
26. stirringThe residue is stirred with 250 ml of isopropanol
27. filtrationfiltered
28. customevaporated under reduced pressure
29. customThe residue is triturated with 250 ml of isopropanol
30. filtrationfiltered
31. customThe filtrate is dried
32. filtrationfiltered
33. customevaporated under reduced pressure
34. stirringAfter trituration, the mixture is stirred in water overnight
35. customthe precipitate then collected
36. customdried in air
37. customThe off-white solid is recrystallized from water yielding 12.10 g of pale yellow crystals which
38. customare dried in vacuo (55° C.), MP 92°- 93° C

ORD record

ord-3fbe8409bf364a599f86c7a7c4daf863

Source dataset

uspto-grants-1987_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04707478