Methanol → 5-(Benzoxazol-2-yl)-1-(4-carboxyphenylmethyl)-2-methylbenzimidazole

HRID 74300Notes

Reaction equation

HRID 74300 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:30]=[CH:29][C:13]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[CH:21][CH:20]=3)[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1.[OH-].[Na+].CO>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:30]=[CH:29][C:13]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=3)[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 674988695-(Benzoxazol-2-yl)-1-(4-methoxycarbonylphenylmethyl)-2-methylbenzimidazole

Product 1

HCID 674986655-(Benzoxazol-2-yl)-1-(4-carboxyphenylmethyl)-2-methylbenzimidazoleYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-(benzoxazol-2-yl)-1-(4-methoxycarbonylphenylmethyl)-2-methylbenzimidazole (see Working Example 113-3) (55 mg, 0.138 mmol) in chloroform (3 mL) was added aqueous sodium hydroxide solution (1 M, 0.6 mL, 0.6 mmol). This two-layer solution was homogenized by the addition of methanol, and this was stirred at room temperature for 20 hours. After the reaction was complete, the solution was concentrated, aqueous acetic acid solution was added, and this was stirred at room temperature. The precipitated crystals were filtered, and after washing with water were dried to yield the title compound (45.9 mg, 87% yield) as yellow crystals.

Workup

  1. concentrationthe solution was concentrated
  2. additionaqueous acetic acid solution was added
  3. stirringthis was stirred at room temperature
  4. filtrationThe precipitated crystals were filtered
  5. washafter washing with water
  6. customwere dried

Sources & evidence

ORD record
ord-b0e92265ff8546aab5cfd7c36b857c83
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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