N,N'-Dimethylurea → 4,5-bis(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-one

HRID 1258269Notes

Reaction equation

HRID 1258269 reaction equation
O[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[CH3:21][NH:22][C:23]([NH:25][CH3:26])=[O:24]>C(O)CO.O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:22]([CH3:21])[C:23](=[O:24])[N:25]([CH3:26])[C:2]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7293N,N'-DimethylureaHCID 954154,4'-Dimethoxybenzoin

Product 1

HCID 593548284,5-bis(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-oneYield 68.5%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-hydroxy-1,2-bis(4-methoxyphenyl)ethanone (1 g, 3.6 mmol) and 1,3-dimethylurea (1.29 g, 14.7 mmol) in ethylene glycol (10 mL) was refluxed at 180° C. for 2 h. The reaction mixture was diluted with water and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, dried over Na2SO4, filtered and then concentrated in vacuo. The crude material was purified via silica gel column chromatography eluting with 80% EtOAc in hexanes to afford 4,5-bis(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-one (0.8 g, 67%) as a solid.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified via silica gel column chromatography
  7. washeluting with 80% EtOAc in hexanes

Sources & evidence

ORD record
ord-a176a8b8bdcf406bb8075b5e8bbdd3be
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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