Dichloromethane → 1-[4-(2-Bromoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

HRID 723336Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[C:9]2=[O:26])=[CH:4][CH:3]=1.[OH-].[Na+].ClCCl.[Br:32][CH2:33][CH2:34]Br>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:32][CH2:33][CH2:34][O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[C:9]2=[O:26])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of 1-(4-hydroxyphenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one (4.7 g) in 1,2-dibromoethane (23.6 ml) was mixed with sodium hydroxide solution (3N, 9.1 ml) and tetrabutylammonium hydrogen sulfate (232 mg). The mixture was heated at 75° C. for 2 hours. After cooling, the reaction mixture was mixed with dichloromethane and washed with sodium hydroxide solution (1N), hydrochloric acid (1N) and saturated brine. 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 451.32 (C23H19BrN2O3); MS (ESI): 451 ([M+H]+), was obtained in this way.

Workup

temperatureAfter cooling
washwashed with sodium hydroxide solution (1N), hydrochloric acid (1N) and saturated brine
dry with materialThe organic phase was dried over magnesium sulfate
concentrationconcentrated
customthe residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 9:1)
customMS (ESI): 451 ([M+H]+), was obtained in this way

Sources & evidence

ORD record: ord-fe892cbda3e64447a214492c064e3981
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141561B2

Reaction notes

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