Hydrochloric Acid → 1h-Benzimidazole-6-acetic acid,1-[(2-chlorophenyl)methyl]-2-methyl-

HRID 1276901Notes

Reaction equation

HRID 1276901 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([CH2:14]C#N)[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:17].Cl.[C:23](=[O:26])([O-])[OH:24].[Na+]>>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([CH2:14][C:23]([OH:24])=[O:26])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 186809811-(2-Chlorobenzyl)-2-methylbenzimidazole-6-acetonitrile

Product 1

HCID 186808611h-Benzimidazole-6-acetic acid,1-[(2-chlorophenyl)methyl]-2-methyl-

Procedure

To 0.500 g of 1-(2-chlorobenzyl)-2-methylbenzimidazole-6-acetonitrile was added 10% hydrochloric acid, and the mixture was heat-refluxed for 15 hours. The reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, and was extracted with chloroform. The organic layer was concentrated, and was purified through silica-gel column chromatography (eluent: a mixture of chloroform and methanol at a ratio of 9:1 to 4:1) to give 0.170 g of 1-(2-chlorobenzyl)-2-methylbenzimidazole-6-acetic acid (160).

Workup

  1. temperaturethe mixture was heat-refluxed for 15 hours
  2. extractionwas extracted with chloroform
  3. concentrationThe organic layer was concentrated
  4. customwas purified through silica-gel column chromatography (eluent
  5. additiona mixture of chloroform and methanol at a ratio of 9:1 to 4:1)

Sources & evidence

ORD record
ord-966a2f8dbab0437ca8799e3f57e0b3d5
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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