Potassium Carbonate → Ethyl 2-[4-(2-bromo-5-chlorobenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

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Reaktionsgleichung

[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4]Br.BrC1C=CC(Cl)=CC=1C.BrN1C(=O)CCC1=O.[CH:28]1([N:34]2[C:38]3[CH:39]=[CH:40][C:41]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:42][C:37]=3[N:36]=[C:35]2[C:48]2[CH:53]=[CH:52][C:51]([OH:54])=[CH:50][CH:49]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4][O:54][C:51]1[CH:52]=[CH:53][C:48]([C:35]2[N:34]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[C:38]3[CH:39]=[CH:40][C:41]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:42][C:37]=3[N:36]=2)=[CH:49][CH:50]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

2-Bromo-5-chlorobenzyl bromide prepared from 2-bromo-5-chlorotoluene (50 g), N-bromosuccinimide and N,N′-azobisisobutyronitrile, and ethyl 1-cyclohexyl-2-(4-hydroxyphenyl)benzimidazole-5-carboxylate (50 g) obtained in Example 3 were suspended in dimethylformamide (300 ml). Potassium carbonate (38 g) was added and the mixture was stirred for 1 hr at 80° C. with heating. The reaction mixture was allowed to cool and then added to a mixed solvent of water-ethyl acetate. The precipitated crystals were collected by filtration to give the title compound (50 g, yield 64%).

Aufarbeitung

temperaturewith heating
temperatureto cool
filtrationThe precipitated crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag: ord-99619a02d4e340f7ae9af021629e18bd
Quelldatensatz: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07285551B2

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