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

HRID 655386

Reaction equation

HRID 655386 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-2c14093d19aa4c4790443352bc3178ce
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Linked notes

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