2-Imidazolidinone → HCID 19045501, compound

HRID 1781404Notes

Reaction equation

HRID 1781404 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].Cl[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:20])=[C:15]([C:17](=[O:19])[CH3:18])[CH:16]=1>CN(C)C=O>[C:17]([C:15]1[CH:16]=[C:11]([CH2:10][N:3]2[CH2:7][CH2:6][NH:5][C:4]2=[O:8])[CH:12]=[CH:13][C:14]=1[OH:20])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 84532-ImidazolidinoneHCID 24758Sodium hydrideHCID 22557013HCID 22557013, compound

Product 1

HCID 19045501HCID 19045501, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 0.80 g, 20.0 mmol) in 15 mL dry dimethylformamide under argon, cooled in an ice-bath was added dropwise a solution of 2-imidazolidone (1.72 g, 20.0 mmol) in 5 mL dimethylformamide. The ice bath was removed, the mixture was stirred 30 minutes and a solution of 5'-chloromethyl-2'-hydroxyacetophenone (1.85 g, 10.0 mmol) in 5 mL dimethylformamide was added dropwise. The mixture was stirred four hours and the product was isolated in the same manner as in the previous example to give a solid. The solid was stirred under 20 mL n-butylchloride, filtered off, and dried in vacuo to give 1.01 g (43%) product as a white solid, mp 131°-133° C.

Workup

  1. temperaturecooled in an ice-bath
  2. customThe ice bath was removed
  3. stirringThe mixture was stirred four hours
  4. customto give a solid
  5. stirringThe solid was stirred under 20 mL n-butylchloride
  6. filtrationfiltered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-dc93e323f5dd4fdea38a1dcf99643bf1
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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