Sodium Hydroxide → HCID 57786580, compound

HRID 1360715Notes

Reaction equation

HRID 1360715 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 (1N). Allowed to stir at r.t. for 48 h. The reddish/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, 6H) 7.14 (d, J=7.58 Hz, 2H) 7.27 (t, J=7.64 Hz, 1H) 7.50 (d, J=8.46 Hz, 0.5H) 7.67 (d, J=8.46 Hz, 0.5H) 7.78 (dd, J=15.09, 8.40 Hz, 1H) 8.03 (s, 0.5H) 8.20 (s, 0.5H) 12.64 (br. s., 1H) 12.85 (d, J=16.29 Hz, 1H). MS (m/z) 267.1 M (+1), tR=0.87, Meth 10

Workup

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

Sources & evidence

ORD record
ord-6afafe071823419987fbd77d6a2ee840
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

Loading…