Sodium Hydroxide → 2-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid

HRID 1360714Notes

Reaction equation

HRID 1360714 reaction equation
C[O:2][C:3]([C:5]1[CH:21]=[CH:20][C:8]2[N:9]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[NH:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>CO>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C:10]1[NH:11][C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:21]=[CH:20][C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 669663062-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 433492922-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Take 2-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester (1.00 g, 3.11 mmol) up in MeOH (6 mL) and 1 N NaOH (6 mL) and stir for 24 hr. Add additional 1 N NaOH (6 mL) and stir for an additional 30 hr. Concentrate under reduced pressure. Neutralize the concentrate at 0° C. by the dropwise addition of 1 N HCl (12 mL). Collect the resulting precipitate and wash with water followed by Et2O. Dry the solid in a vac oven to afford the desired acid as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.60-7.67 (m, 1H) 7.68 (s, 2H) 7.70 (d, J=2.15 Hz, 1H) 7.89 (d, J=8.46 Hz, 1H) 8.24 (br. s., 1H) 12.83 (br. s., 1H) 13.23 (br. s., 1H); (M+H)+ 306.9.

Workup

  1. stirringstir for an additional 30 hr
  2. concentrationConcentrate under reduced pressure
  3. concentrationconcentrate at 0° C. by the dropwise addition of 1 N HCl (12 mL)
  4. customCollect the resulting precipitate
  5. washwash with water
  6. customDry the solid in a vac oven

Sources & evidence

ORD record
ord-47d615cb30ac460593b82e1dee01c0e8
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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