Sodium hydride → HCID 57006706, compound

HRID 2287334Notes

Reaction equation

HRID 2287334 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+].Br[CH2:18][CH2:19][CH2:20][CH2:21][Cl:22]>CN(C)C=O>[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][CH2:12][N:11]([CH2:18][CH2:19][CH2:20][CH2:21][Cl:22])[C:10]2=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 19261677HCID 19261677, compound

Product 1

HCID 57006706HCID 57006706, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 1-phenylmethylenamino-2-imidazolidinone (27.6 g, 0.1458 mole) [prepared as in Example A, Part II] in dimethylformamide (500 ml) is treated portionwise with 60% NaH in mineral oil (5.8 g, 0.1458 mole) over 30 minutes. The resulting mixture is stirred at ambient temperature 30 minutes, then heated at 80-90° C. for 30 minutes. The resulting thick mixture is cooled to ambient temperature, and 1-bromo-4-chlorobutane (50.0 g, 0.2916 mole, 2 eq) is added in one portion. The mixture is heated at 80°-90° C. After 30 minutes, a near-solution is formed followed, by gradual precipitation of a small amount of solid. The mixture is heated at 80°-90° C. temperature for 3 hours, then stirred at ambient temperature for 18 hours. The mixture is filtered (celite) removing a small amount of insoluble material. The filtrate is concentrated under reduced pressure to an oily residue. This residue is triturated with H2O giving a solid. The solid is collected and air-dried. This solid is triturated by stirring in anhydrous ether (350 ml) for one hour. The solid is collected and air-dried to give 36.4 g (0.130 mole) of 1-phenylmethyleneamino-3-(4-chlorobutyl)-2-imidazolidinone.

Workup

  1. temperatureheated at 80-90° C. for 30 minutes
  2. temperatureThe resulting thick mixture is cooled to ambient temperature
  3. temperatureThe mixture is heated at 80°-90° C
  4. waitAfter 30 minutes
  5. customa near-solution is formed
  6. customfollowed, by gradual precipitation of a small amount of solid
  7. temperatureThe mixture is heated at 80°-90° C. temperature for 3 hours
  8. stirringstirred at ambient temperature for 18 hours
  9. filtrationThe mixture is filtered (celite)
  10. customremoving a small amount of insoluble material
  11. concentrationThe filtrate is concentrated under reduced pressure to an oily residue
  12. customThis residue is triturated with H2O giving a solid
  13. customThe solid is collected
  14. customair-dried
  15. customThis solid is triturated
  16. stirringby stirring in anhydrous ether (350 ml) for one hour
  17. customThe solid is collected
  18. customair-dried

Sources & evidence

ORD record
ord-f377fa0befd84e40a0e56e2952239b3a
Source dataset
uspto-grants-2000_07
Patent number
US06083945

Reaction notes

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