Hydrochloric Acid → HCID 58924865, compound

HRID 1990988Notes

Reaction equation

HRID 1990988 reaction equation
[OH:1][CH2:2][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.[Li+].[OH-].Cl>C1COCC1.O>[OH:1][CH2:2][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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58924938HCID 58924938, compound

Product 1

HCID 58924865HCID 58924865, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-hydroxymethyl-phenyl)-thiazole-4-carboxylic acid, ethyl ester (1.3 g) in THF (5 mL) was added an aqueous solution of LiOH:H2O (472 mg in 5 mL water) and the resulting biphasic mixture was stirred vigorously at room temperature for 3 h. The reaction mixture was then acidified with 1N HCl, diluted with water and extracted three times with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and then concentrated. The crude product was dissolved in a small amount of ethyl acetate and precipitated by addition of hexanes to give 2-(2-hydroxymethyl-phenyl)-thiazole-4-carboxylic acid (926 mg) as a light yellow solid. HRMS calcd for Cl1H9NO3S (M+) 235.0303, observed 235.0302.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. dissolutionThe crude product was dissolved in a small amount of ethyl acetate
  5. customprecipitated by addition of hexanes

Sources & evidence

ORD record
ord-66cc0e68629744e1a087980f0aaac2f0
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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