Sodium Hydroxide → 2-(3-Methoxyphenyl)-1,3-thiazole-4-carboxylic acid

HRID 460185Notes

Reaction equation

HRID 460185 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[S:10][CH:11]=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15170573Ethyl 2-(3-methoxyphenyl)thiazole-4-carboxylate

Product 1

HCID 156230652-(3-Methoxyphenyl)-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of the ethyl 2-(3-methoxy-phenyl)thiazole-4-carboxylate (0.23 g, 0.87 mmol) in EtOH (10 mL) was added 1N NaOH (aq) (5 mL). The resulting mixture was heated to reflux until the starting material was consumed (2 h). The mixture was cooled to RT, acidified with 1N HCl (aq) and concentrated by rotary evaporation. The residue was extracted with CH2Cl2 (3×15 mL). The extracts were combined, dried over MgSO4, filtered and concentrated by rotary evaporation to afford the title compound as an off-white solid. EI-MS m/z 236 (M+H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux until the starting material
  3. customwas consumed (2 h)
  4. concentrationconcentrated by rotary evaporation
  5. extractionThe residue was extracted with CH2Cl2 (3×15 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-b13cfeaa11544d3e9c6dda4864f8db1d
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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