Water → 2-(5,6-Dimethoxybenzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid

HRID 1785481Notes

Reaction equation

HRID 1785481 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([O:22][CH3:23])[C:18]([O:20][CH3:21])=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:5])C.[OH-].[Na+].O>C1COCC1>[CH3:21][O:20][C:18]1[C:17]([O:22][CH3:23])=[CH:16][C:15]2[N:11]([C:9]3[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:8]=3)[CH:12]=[N:13][C:14]=2[CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 24886662HCID 24886662, compound

Product 1

HCID 236536592-(5,6-Dimethoxybenzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(5,6-Dimethoxybenzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid ethyl ester (180 mg, 0.44 mmol) was suspended in THF (4 ml), NaOH (15%, 1.5 ml) and water (2 ml) and the mixture was stirred at 40-50° C. for 3 hrs. After THF was removed, the residue was extracted with ethyl acetate (2×2 mL). The aqueous was then neutralized with 3N HCl to pH=3. The solid was collected by filtration and was washed with water, dried in airflow to give 2-(5,6-Dimethoxybenzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid (147 mg, 0.38 mmol, 88%). 1H-NMR (DMSO-D6) 8.74 (s, 1H); 7.80 (s, 1H); 7.57-7.63 (m, 2H); 7.40-7.56 (m, 3H); 7.38 (s, 1H); 3.83 (d, 6H). MS M/z 382 (M+1).

Workup

  1. customAfter THF was removed
  2. extractionthe residue was extracted with ethyl acetate (2×2 mL)
  3. filtrationThe solid was collected by filtration
  4. washwas washed with water
  5. customdried in airflow

Sources & evidence

ORD record
ord-8df2b2f2ab9843b1ad9a8483dab5bafd
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

Loading…