Sodium Hydroxide → HCID 21876016, compound

HRID 858461Notes

Reaction equation

HRID 858461 reaction equation
[Cl:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]2[N:6]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]CC)=[O:19])=[CH:13][CH:12]=3)[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[C:24]([Cl:25])=[CH:23][C:5]2[N:6]([C:11]3[CH:12]=[CH:13][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:15][CH:16]=3)[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86611498HCID 86611498, compound

Product 1

HCID 21876016HCID 21876016, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl [4-(5,6-dichloro-2-ethyl-1H-benzimidazol-1-yl)phenyl]acetate (step 3, 1.30 g, 3.4 mmol) in methanol was added 2N aqueous NaOH (3.4 mL) at room temperature. After 1 h, the mixture was concentrated and the residue was diluted in water (200 mL) and the mixture was washed with diethyl ether (100 mL). The aqueous layer was acidified with 2N hydrochloric acid and extracted with ethyl acetate/THF (v/v, 1:1, 300 mL). The organic extract was washed with water (200 mL), brine (200 mL), and dried (MgSO4). Removal of solvent gave 1.02 g (86%) of the title compound as a white powder: 1H-NMR (CDCl3) δ 7.94 (1H, s), 7.56–7.45 (4H, m), 7.26 (1H, s), 3.72 (2H, s), 2.72 (2H, q, J=7.3 Hz), 1.22 (3H, t, J=7.5 Hz).

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe residue was diluted in water (200 mL)
  3. washthe mixture was washed with diethyl ether (100 mL)
  4. extractionextracted with ethyl acetate/THF (v/v, 1:1, 300 mL)
  5. extractionThe organic extract
  6. washwas washed with water (200 mL), brine (200 mL)
  7. dry with materialdried (MgSO4)
  8. customRemoval of solvent

Sources & evidence

ORD record
ord-ba561e30b15b46fe8757b863d956e498
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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