Sodium Hydroxide → HCID 67087925, compound

HRID 2175699Notes

Reaction equation

HRID 2175699 reaction equation
[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][C:6]2[NH:7][C:8]([C:10]([NH:12][C:13]3[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=3[C:15]([O:17]C)=[O:16])=[O:11])=[N:9][C:5]=2[CH:4]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][C:6]2[NH:7][C:8]([C:10]([NH:12][C:13]3[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=3[C:15]([OH:17])=[O:16])=[O:11])=[N:9][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67087802HCID 67087802, compound

Product 1

HCID 67087925HCID 67087925, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(5,6-dimethoxy-1H-benzo[d]imidazole-2-carboxamido)benzoate (200 mg, 0.56 mmol) in THF (10 mL) and MeOH (5 mL) was added 2N NaOH solution (1.4 mL) dropwise. The resulting mixture was stirred at room temperature for 2 hours. The reaction was quenched by addition of 1N HCl solution and extracted with DCM. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give 2-(5,6-dimethoxy-1H-benzo[d]imidazole-2-carboxamido)benzoic acid (90 mg, 47.1%). 1H-NMR (400 MHz, DMSO-d6) δ 3.82 (s, 6H), 6.97 (s, 1H), 7.13-7.34 (m, 2H), 7.64 (m, 1H), 8.08 (d, J=9.6 Hz, 1H), 8.78 (d, J=7.6 Hz; 1H), 12.90 (s, 1H), 13.27 (s, 1H); LC-MS (ES-API); rt 8.74 min; m/z calculated for C17H15N3O5 [M−H]− 340.1, found 340.1.

Workup

  1. customThe reaction was quenched by addition of 1N HCl solution
  2. extractionextracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c186d085bbb34dfe8cae5c13fe3fe4cc
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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