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

HRID 1425807Notes

Reaction equation

HRID 1425807 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-e2ddb94302e84d259659583d1090f909
Source dataset
uspto-grants-2015_01
Patent number
US08933074B2

Reaction notes

Loading…