Hydrochloric Acid → 2-(2-Methoxyphenyl)-1,3-thiazole-4-carboxylic acid

HRID 460187Notes

Reaction equation

HRID 460187 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=1.[OH-].[Na+].Cl>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10015624Ethyl 2-(2-methoxyphenyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 156230682-(2-Methoxyphenyl)-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 2-(2-methoxy-phenyl)thiazole-4-carboxylate (0.27 g, 1.03 mmol) in EtOH (10 mL) was added 1N NaOH (aq) (5 mL). The resulting mixture was heated to reflux for 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 for 2 h
  3. concentrationconcentrated by rotary evaporation
  4. extractionThe residue was extracted with CH2Cl2 (3×15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-ef70904d91a04535ab151a5902302ed4
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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