Sodium Iodide → HCID 70173092, compound

HRID 2211133Notes

Reaction equation

HRID 2211133 reaction equation
[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][C:12](=[O:14])[N:11]([CH2:15][CH2:16][CH2:17][CH2:18]Cl)[C:10]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-:21].[Na+]>CC(C)=O>[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][C:12](=[O:14])[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][I:21])[C:10]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 70173102HCID 70173102, compound

Product 1

HCID 70173092HCID 70173092, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-phenylmethyleneamino-3-(4-chlorobutyl)-2,4 imidazolidinedione (prepared as described in Part I above) (43.1 g, 0.1467 mole), acetone (1200 ml) and sodium iodide (48.4 g, 0.3227 mole) is heated to reflux. Reflux is maintained for 5 hours. The mixture is filtered, collecting the insoluble. The filtrate is recharged with sodium iodide (10 g) and reflux is resumed and is maintained for 15 hours. After cooling to ambient temperature, the mixture is filtered, removing the insoluble NaCl (total recovery, 9.5 g, 110%). The filtrate is poured into H2O (2000 ml) while stirring. After stirring for 30 minutes, the solid is collected and air-dried to yield 51.5 g (0.1337 mole) of 1-phenylmethyleneamino-3-(4-iodobutyl)-2,4-imidazolidinedione.

Workup

  1. temperatureis heated to reflux
  2. temperatureReflux
  3. temperatureis maintained for 5 hours
  4. filtrationThe mixture is filtered
  5. customcollecting the insoluble
  6. temperaturereflux
  7. temperatureis maintained for 15 hours
  8. filtrationthe mixture is filtered
  9. customremoving the insoluble NaCl (total recovery, 9.5 g, 110%)
  10. additionThe filtrate is poured into H2O (2000 ml)
  11. stirringAfter stirring for 30 minutes
  12. customthe solid is collected
  13. customair-dried

Sources & evidence

ORD record
ord-74edc5855400403982a328091948851b
Source dataset
uspto-grants-1995_10
Patent number
US05462940

Reaction notes

Loading…