Sodium Hydroxide → 4-(5,6-dichloro-1H-benzimidazol-2-yl)benzoic acid

HRID 1352656Notes

Reaction equation

HRID 1352656 reaction equation
[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11][CH:10]=3)[NH:8][C:4]=2[CH:3]=1.[OH-].[Na+]>C1COCC1>[Cl:21][C:20]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]=[C:7]([C:9]3[CH:10]=[CH:11][C:12]([C:15]([OH:17])=[O:16])=[CH:13][CH:14]=3)[NH:6][C:5]=2[CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21101171HCID 21101171, compound

Product 1

HCID 40731194-(5,6-dichloro-1H-benzimidazol-2-yl)benzoic acidYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5,6-dichloro-2-(4-methoxycarbonylphenyl)benzimidazole (2.4 g, 7.47 mmol), prepared as described in Preparation 7, 20% NaOH (7.5 ml, 37.5 mmol) in THF (25 ml) was heated at 50° C. for 1 h. After cooling at room temperature, solvent was removed under reduced pressure and pH was adjusted to 5 with acetic acid. The solid that was precipitated was filtered and dried at 50° C. to give 2.1 g of the title compound (yield 91.8%) as a brown solid, mp>250° C.

Workup

  1. customprepared
  2. temperatureAfter cooling at room temperature
  3. customsolvent was removed under reduced pressure and pH
  4. customThe solid that was precipitated
  5. filtrationwas filtered
  6. customdried at 50° C.

Sources & evidence

ORD record
ord-7223f598e4994bda884043da906bdf42
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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