Sodium Hydroxide → HCID 15284923, compound

HRID 1974446Notes

Reaction equation

HRID 1974446 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:20][CH2:19][CH2:18][CH:17]3[C:21]([O:23]C)=[O:22])=[CH:12][CH:11]=2)[C:7]2[CH:25]=[CH:26][CH:27]=[CH:28][C:6]=2[N:5]=1)[CH2:2][CH3:3].[OH-].[Na+]>CO>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:20][CH2:19][CH2:18][CH:17]3[C:21]([OH:23])=[O:22])=[CH:12][CH:11]=2)[C:7]2[CH:25]=[CH:26][CH:27]=[CH:28][C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15284922HCID 15284922, compound

Product 1

HCID 15284923HCID 15284923, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-[4-[(2-propyl-1H-benzimidazol-1-yl)methyl]phenyl]cyclopentane-1-carboxylate (530 mg, 1.41 mmol), 1N NaOH (2.8 mL), and MeOH (5.0 mL) was heated under reflux for 6 h. The mixture was concentrated, diluted with water (10 mL), and extracted with ether (discarded). The aqueous phase was neutralized with 1N HCl (2.8 mL) and the white precipitate was collected by filtration. Recrystallization from EtOH gave 320 mg (63%) of product, mp 179°-180° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. concentrationThe mixture was concentrated
  4. additiondiluted with water (10 mL)
  5. extractionextracted with ether (discarded)
  6. filtrationthe white precipitate was collected by filtration
  7. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-592f12d062944fc0a76cdd99d5cea8c3
Source dataset
uspto-grants-1994_02
Patent number
US05283242

Reaction notes

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