1,2-Dibromoethane → HCID 12095857, compound

HRID 723332Notes

Reaction equation

[CH2:1]([C:8]1[CH:9]=[C:10]([N:15]2[CH:19]=[CH:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][CH:21]=3)[C:16]2=[O:33])[CH:11]=[CH:12][C:13]=1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Br:36][CH2:37][CH2:38]Br>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:1]([C:8]1[CH:9]=[C:10]([N:15]2[CH:19]=[CH:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][CH:21]=3)[C:16]2=[O:33])[CH:11]=[CH:12][C:13]=1[O:14][CH2:38][CH2:37][Br:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 1-(3-benzyl-4-hydroxyphenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one (233 mg) in 1,2-dibromoethane (1.7 ml) was mixed with sodium hydroxide solution (3N, 0.6 ml) and tetrabutylammonium hydrogen sulfate (12 mg). The mixture was heated at 80° C. for 2 hours. After cooling, the reaction mixture was diluted 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: heptane/ethyl acetate 3:2). The product with the molecular weight of 541.45 (C30H25BrN2O3); MS (ESI): 541 ([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: heptane/ethyl acetate 3:2)
customMS (ESI): 541 ([M+H]+), was obtained in this way

Sources & evidence

ORD record: ord-3659f3e972a34bb8b6bbb10007faa8b8
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141561B2

Reaction notes

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