Sodium hydride → HCID 53728677, compound

HRID 2287332Notes

Reaction equation

HRID 2287332 reaction equation
[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:17][N:18]([CH2:20][CH2:21][CH2:22]Cl)[CH3:19]>CN(C)C=O>[CH3:17][N:18]([CH3:19])[CH2:20][CH2:21][CH2:22][N:11]1[CH2:12][CH2:13][N:9]([N:8]=[CH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:10]1=[O:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 19261677HCID 19261677, compound

Product 1

HCID 53728677HCID 53728677, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A near solution of 9.46 g (0.050 mole) of 1-[(phenyl methylene)amino]-2-imidazolidinone in 125 ml of dimethylformamide is treated portionwise with 2.0 g (0.050 mole) of NaH (60% dispersion in mineral oil) with the temperature rising to 30° C. The reaction is stirred at ambient temperature for 15 minutes with a solid forming. A 100 ml portion of dimethylformamide is added, to aid in stirring, and the mixture is stirred at 80° to 90° C. for 30 minutes. The mixture is cooled to ambient temperature and treated all at once with 12.2 g (0.100 mole) of dimethylaminopropyl chloride (prepared as described in Part I above). The resulting mixture is heated at 80° to 90° C. for 3 hours with near dissolution. The solvent is removed in vacuo. The residual semi-solid is dissolved in H2O (150 ml), and extracted with ethyl acetate (2×200 ml). The combined extracts are dried over MgSO4 and the solvent is removed in vacuo. The residual solid is washed with ether and air-dried to yield 4.8 g of 3-[3-(dimethylamino)propyl]-1-[(phenylmethylene)amino]-2-imidazolidinone.

Workup

  1. customrising to 30° C
  2. customforming
  3. stirringin stirring
  4. stirringthe mixture is stirred at 80° to 90° C. for 30 minutes
  5. temperatureThe mixture is cooled to ambient temperature
  6. temperatureThe resulting mixture is heated at 80° to 90° C. for 3 hours with near dissolution
  7. customThe solvent is removed in vacuo
  8. dissolutionThe residual semi-solid is dissolved in H2O (150 ml)
  9. extractionextracted with ethyl acetate (2×200 ml)
  10. dry with materialThe combined extracts are dried over MgSO4
  11. customthe solvent is removed in vacuo
  12. washThe residual solid is washed with ether
  13. customair-dried

Sources & evidence

ORD record
ord-cbd4ef3f6a7541e0a3e578ee2a1b9b41
Source dataset
uspto-grants-2000_07
Patent number
US06083945

Reaction notes

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