Hydrochloric Acid → HCID 14953100, compound

HRID 893357Notes

Reaction equation

HRID 893357 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][C:18]([CH3:26])([CH3:25])[CH2:19][C:20]([O:22]CC)=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>C(O)(=O)C>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][C:18]([CH3:26])([CH3:25])[CH2:19][C:20]([OH:22])=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 14953037HCID 14953037, compound

Product 1

HCID 14953100HCID 14953100, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9 g of ethyl 4-(1-benzylbenzimidazol-2-yl)-3,3-dimethylbutanoate, prepared in Example 47, are dissolved in a mixture composed of 90 ml of concentrated hydrochloric acid, 270 ml of water and 250 ml of acetic acid. The mixture is refluxed for 4 hours and the solvents are concentrated under vacuum. The residue is taken up with a 1N solution of sodium hydroxide and the resulting mixture is washed with ether; the aqueous phase is acidified by having sulfur dioxide bubbled through it until the pH is 5-6, and the crystals formed are filtered off and washed with water and isopropyl ether to give 5.3 g of 4-(1-benzylbenzimidazol-2-yl)-3,3-dimethylbutanoic acid in the form of crystals melting at 160°-1° C.

Workup

  1. dissolutionare dissolved in a mixture
  2. temperatureThe mixture is refluxed for 4 hours
  3. concentrationthe solvents are concentrated under vacuum
  4. washthe resulting mixture is washed with ether
  5. custombubbled through it until the pH is 5-6
  6. customthe crystals formed
  7. filtrationare filtered off
  8. washwashed with water and isopropyl ether

Sources & evidence

ORD record
ord-81059773e27d44579020757928414bec
Source dataset
uspto-grants-1992_06
Patent number
US05124336

Reaction notes

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