Sodium Hydroxide → HCID 57786580, compound

HRID 1513213Notes

Reaction equation

HRID 1513213 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]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])[NH:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>CO>[CH3:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[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 HydroxideHCID 66965285HCID 66965285, compound

Product 1

HCID 57786580HCID 57786580, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a tan suspension of 7.23 g (25.8 mmol) of 2-(2,6-Dimethyl-phenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester in 50 mL MeOH was added 80 mL of NaOH (1 N). Allowed to stir at r.t. for 48 h. The redish/brown solution was dried, and to the residue was added 50 mL water, and brought to pH 4. Solid was filtered off to give near quantitative yield of title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.03 (s, 6 H) 7.14 (d, J=7.58 Hz, 2 H) 7.27 (t, J=7.64 Hz, 1 H) 7.50 (d, J=8.46 Hz, 0.5 H) 7.67 (d, J=8.46 Hz, 0.5 H) 7.78 (dd, J=15.09, 8.40 Hz, 1 H) 8.03 (s, 0.5 H) 8.20 (s, 0.5 H) 12.64 (br. s., 1 H) 12.85 (d, J=16.29 Hz, 1 H). MS (m/z) 267.1 M (+1), tR=0.87, Meth 10

Workup

  1. customThe redish/brown solution was dried
  2. additionto the residue was added 50 mL water
  3. filtrationSolid was filtered off

Sources & evidence

ORD record
ord-967c0f8145544595bcb8cab64d1e01d2
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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