Sodium hydride → HCID 70173102, compound

HRID 2211132Notes

Reaction equation

HRID 2211132 reaction equation
[H-].[Na+].[CH:3](=[N:10][N:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23]>CN(C)C=O>[ClH:23].[ClH:23].[C:4]1([CH:3]=[N:10][N:11]2[CH2:17][C:15](=[O:16])[N:14]([CH2:19][CH2:20][CH2:21][CH2:22][Cl:23])[C:12]2=[O:13])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[C:4]1([CH:3]=[N:10][N:11]2[CH2:17][C:15](=[O:16])[N:14]([CH2:19][CH2:20][CH2:21][CH2:22][Cl:23])[C:12]2=[O:13])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 819014HCID 819014, compound

Product 2

HCID 70173102HCID 70173102, compoundHCID 70173128HCID 70173128, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-Phenylmethylenamino-3-(4-chlorobutyl)-2,4-imidazolidinedione dihydrochloride is prepared by adding 60% sodium hydride in mineral oil (7.8 g, 0.1944 mole) over 1 hour to a stirred solution of 1-(benzylideneamino)hydantoin [prepared as described by J. Gut, A Novacet, and P. Fiedler, Coll. Czech. Chem. Commun., Vol. 33, pp. 2087-2096 (No. 7). 1968 hereby incorporated by reference herein] (39.5 g, 0.1944 mole) in dimethylformamide (1000 ml). After complete addition, the solution is heated at steam bath temperature (approximately 100° C.) for 1.5 hours. The resulting mixture is allowed to cool to ambient temperature (30° C.). While stirring at ambient temperature, 1-bromo-4-chlorobutane (100 g, 0.5832 mole, 3 eq) is added in one portion. The mixture becomes exothermic reaching around 35° C. in approximately 30 minutes. The near-solution is heated at approximately 80° C. by steam bath for four hours, cooled and stirred for approximately eight hours at ambient temperature (30° C.). The cloudy mixture is filtered, removing a small amount of insoluble solid. The filtrate is concentrated under reduced pressure to a semi-solid residue. This residue is triturated with H2O (400 ml), collected, recrystallized from acetonitrile, and then air-dried to give 43.1 g (0.1467 mole) of 1-phenylmethyleneamino-3-(4-chlorobutyl)-2,4-imidazolidinedione.

Workup

  1. customprepared
  2. additionAfter complete addition
  3. temperatureto cool to ambient temperature (30° C.)
  4. temperatureThe near-solution is heated at approximately 80° C. by steam bath for four hours
  5. temperaturecooled
  6. stirringstirred for approximately eight hours at ambient temperature (30° C.)
  7. filtrationThe cloudy mixture is filtered
  8. customremoving a small amount of insoluble solid
  9. concentrationThe filtrate is concentrated under reduced pressure to a semi-solid residue
  10. customThis residue is triturated with H2O (400 ml)
  11. customcollected
  12. customrecrystallized from acetonitrile
  13. customair-dried

Sources & evidence

ORD record
ord-58e579dd44cd4cfcafe462c35910bda9
Source dataset
uspto-grants-1995_10
Patent number
US05462940

Reaction notes

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