Sodium Hydroxide → 2-Oxo-2,3-dihydro-1,3-thiazole-5-carboxylic acid

HRID 1480389Notes

Reaction equation

HRID 1480389 reaction equation
C[O:2][C:3]1[S:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][N:7]=1.C[O-].[Na+].[OH-].[Na+]>CO>[O:2]=[C:3]1[NH:7][CH:6]=[C:5]([C:8]([OH:10])=[O:9])[S:4]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 164948972-Methoxy-1,3-thiazole-5-carboxylic acid

Product 1

HCID 200616172-Oxo-2,3-dihydro-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Methoxythiazole-5-carboxylic acid (step 1) (45.5 mg, 0.286 mmol) was solubilised in MeOH (2 ml) and treated with 5.4M NaOMe in MeOH (212 μl, 1.143 mmol) followed by 2M NaOH (572 μl, 1.143 mmol). The reaction mixture was refluxed overnight and after cooling to RT, the solvent was evaporated under reduced pressure. The residue was acidified with 6M aqueous hydrochloric acid and aqueous layer extracted with EtOAc. The organics were combined and dried over MgSO4 (anh) filtered and evaporated under reduced pressure resulting in a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customthe solvent was evaporated under reduced pressure
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4 (anh)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customresulting in a pale yellow solid

Sources & evidence

ORD record
ord-03721ea365104971b353daf8f98bb2bd
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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