Sodium Carbonate → 1-(4-Hydroxyphenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

HRID 723333Notes

Reaction equation

HRID 723333 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:37])[N:17]([CH2:31][CH:32](OC)OC)[C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:32]=[CH:31][N:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:20][CH:19]=3)[C:16]2=[O:37])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 218733223-(4-Benzyloxyphenyl)-1-(2,2-dimethoxyethyl)-1-(4-phenoxyphenyl)urea

Product 1

HCID 218734101-(4-Hydroxyphenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(4-benzyloxyphenyl)-1-(2,2-dimethoxyethyl)-1-(4-phenoxy-phenyl)urea (498 mg) in trifluoroacetic acid (5 ml) was left to stand for 3 days and then neutralized with saturated sodium carbonate solution. The mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated, and the residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 9:1). The product with the molecular weight of 434.50 (C28H22N2O3); MS (ESI): 435 ([M+H]+), was obtained in this way. 1-(4-Hydroxyphenyl)-3-(4-phenoxy-phenyl)-1,3-dihydroimidazol-2-one was obtained as a further product.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 9:1)
  5. customMS (ESI): 435 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-ee16078822834e5d93d28dacb63ce7d1
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

Loading…