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

HRID 1882902Notes

Reaction equation

HRID 1882902 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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)].

Workup

  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

Sources & evidence

ORD record
ord-dc6bcb4f152a47cd8f74a9b579706cdf
Source dataset
uspto-grants-2004_07
Patent number
US06759425B2

Reaction notes

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