Methane → 2-(4-Carboxyphenyl)-1H-benzimidazole-6-carboxylic acid

HRID 1180585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180585
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13]3[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-].C>C1COCC1.O>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:12][C:13]3[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:9][CH:10]=1)([OH:4])=[O:2]

Komponenten

6

Edukt 3

HCID 297MethaneHCID 3939Lithium HydroxideHCID 160843592-[4-(Methoxycarbonyl)phenyl]-1H-benzimidazole-6-carboxylic acid

Produkt 1

HCID 49154222-(4-Carboxyphenyl)-1H-benzimidazole-6-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-methoxycarbonyl-phenyl)-3H-benzoimidazole-5-carboxylic acid (4.1 g) in THF (15 mL) and water (18 mL) and LiOH (1.74 g) was stirred for 16 hours at room temperature and then mixed with hot water (100 mL) and charcoal. The mixture was filtered and the filtrate was diluted with ice and water (100 mL) and acidified with conc. HCl. The crude diacid was filtered, washed with water and ether and then recrystallized from THF and MeOH. Yield 3.3 g; TLC single spot [CH2Cl2—CH3OH (9:1)].

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with ice and water (100 mL)
  3. filtrationThe crude diacid was filtered
  4. washwashed with water and ether
  5. customrecrystallized from THF and MeOH

Quellen und Nachweise

ORD-Eintrag
ord-93e21a5314a74a0eb60270fa3e034b29
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282518B2

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