1-Imidazolidinecarboxylic acid, 2,5-dioxo-4,4-diphenyl-, ethyl ester → HCID 20329017, compound

HRID 2052062Notes

Reaction equation

HRID 2052062 reaction equation
[H-].[Na+].C([N:8]1[C:12](=[O:13])[C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:10][C:9]1=[O:26])(OCC)=O.[H][H].C([O:31][C:32](=[O:38])[CH2:33][CH2:34][CH2:35][CH2:36]Br)C>CN(C)C=O.[OH-].[Na+]>[C:32]([CH2:33][CH2:34][CH2:35][CH2:36][N:10]1[C:11]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:12](=[O:13])[NH:8][C:9]1=[O:26])([OH:38])=[O:31]

Participants

7

Reactant 4

HCID 141881-Imidazolidinecarboxylic acid, 2,5-dioxo-4,4-diphenyl-, ethyl esterHCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 178418361HCID 178418361, compound

Product 1

HCID 20329017HCID 20329017, compoundYield 15.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

Under an argon atmosphere, 4.32 g (0.09 mol) of sodium hydride (50% dispersion in mineral oil) was placed in a dry, 1 liter, 3-necked round bottom flask equipped with a mechanical stirrer and thermometer. The sodium hydride was rinsed with 250 ml of dry hexane. To the washed material was added 29 g (0.09 mol) of 3-carbethoxy-5,5-diphenylhydantoin (1) [L. Call, Monat. Chem. 101:228(1970)] dissolved in 250 ml of dry dimethylformamide (DMF). After stirring for one hour, hydrogen gas evolution ceased. Then 20.9 g (0.1 mol) of ethyl-5-bromovalerate was added and the reaction stirred overnight at room temperature. The DMF was removed under high vacuum and the residue partitioned between 500 ml of ether and 300 ml of water (H2O). The ether phase was separated, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and evaporated to give an oil. This oil was stirred at 5° C. for 3 hours in 500 ml of 2 N sodium hydroxide. Acidification with dilute hydrochloric acid precipitated an oil that was crystallized from ether and recrystallized from aqueous methanol to give 5 g of 1-(4-carboxybutyl)-5,5-diphenylhydantoin (4) as white crystals, mp 207° C.

Workup

  1. customequipped with a mechanical stirrer
  2. washThe sodium hydride was rinsed with 250 ml of dry hexane
  3. stirringthe reaction stirred overnight at room temperature
  4. customThe DMF was removed under high vacuum
  5. customthe residue partitioned between 500 ml of ether and 300 ml of water (H2O)
  6. customThe ether phase was separated
  7. washwashed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customto give an oil
  12. customAcidification with dilute hydrochloric acid precipitated an oil that
  13. customwas crystallized from ether
  14. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-c49b2f969096415aa0e1ed65a38046d5
Source dataset
uspto-grants-1980_01
Patent number
US04182856

Reaction notes

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