Sodium Hydroxide → 2-[4-(3-Bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylic acid

HRID 1181313

Reaktionsgleichung

Reaktionsgleichung von HRID 1181313
[Br:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:15]3[CH:23]=[CH:24][C:25]([C:27]([O:29]CC)=[O:28])=[CH:26][C:14]=3[N:13]=2)=[CH:8][CH:7]=1.[OH-].[Na+]>O1CCCC1.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:15]3[CH:23]=[CH:24][C:25]([C:27]([OH:29])=[O:28])=[CH:26][C:14]=3[N:13]=2)=[CH:8][CH:7]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 9914616Ethyl 2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

Produkt 1

HCID 102067052-[4-(3-Bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 2-[4-(3-bromophenoxy)phenyl]-1-cyclohexyl-benzimidazole-5-carboxylate (1.0 g) obtained in Example 1 was dissolved in tetrahydrofuran (10 ml) and ethyl alcohol (10 ml), and 4N sodium hydroxide (10 ml) was added. The mixture was refluxed under heating for 1 hr. The reaction mixture was concentrated under reduced pressure and water was added to the residue. The mixture was acidified with 6N hydrochloric acid and the precipitated crystals were collected by filtration to give the title compound (0.9 g, yield 96%).

Aufarbeitung

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure and water
  4. additionwas added to the residue
  5. filtrationthe precipitated crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-9945308b5c234ab7a5dc95c043624e11
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285551B2

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