Sodium Iodide → HCID 131719164, compound

A stirred solution of 1-[[[5-(4-chlorophenyl)-2-furanyl]methlene]amino]-3-(4-chlorobutyl)-2,4-imidazolidinedione (5.0 g, 0.0127 mole), (prepared and described above), dimethylformamide (150 ml), sodium iodide (3.8 g, 0.0254 mole), K2CO3 (1.76 g, 0.0127 mole) and 4-piperidineethanol (4.1 g, 0.0318) is heated on a steam bath for 1.5 hour. After cooling, the mixture is concentrated under reduced pressure to a semi-solid residue. This residue is suspended in H2O (300 ml) and is then extracted with CH2Cl2. The extract is washed with H2O (3×100 ml) then dried over MgSO4 (activated charcoal). The filtered solution is concentrated under reduced pressure to a solid residue. This is triturated with anhydrous ether, collected, and air-dried. This solid is dissolved in absolute EtOH (300 ml) with warming, cooled and made acidic with EtOH/HCl. After cooling on ice several hours, the solid is collected, washed with anhydrous ether, air-dried and dried at 70° to give 4.05 g (0.077 mole) of (4-chlorophenyl)-2-furanyl]methylene]amino]-3-[4-[4-(2-hydroxyethyl)piperidinyl]butyl]-2,4-imidazolidinedione hydrochloride.

1. temperatureAfter cooling
2. concentrationthe mixture is concentrated under reduced pressure to a semi-solid residue
3. extractionis then extracted with CH2Cl2
4. washThe extract is washed with H2O (3×100 ml)
5. dry with materialthen dried over MgSO4 (activated charcoal)
6. concentrationThe filtered solution is concentrated under reduced pressure to a solid residue
7. customThis is triturated with anhydrous ether
8. customcollected
9. customair-dried
10. dissolutionThis solid is dissolved in absolute EtOH (300 ml)
11. temperaturewith warming
12. temperaturecooled
13. temperatureAfter cooling on ice several hours
14. customthe solid is collected
15. washwashed with anhydrous ether
16. customair-dried
17. customdried at 70°

ORD record

ord-0403b47cd3a540e5a6dc6506cdb1f3a9

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05462940