Sodium Hydroxide → 5-Thiazolecarboxylic acid, 2-ethyl-

HRID 70904Notes

Reaction equation

HRID 70904 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([C:8]([O:10]CC)=[O:9])=[CH:6][N:7]=1)[CH3:2].[OH-].[Na+]>CO>[CH2:1]([C:3]1[S:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57438029Ethyl 2-ethylthiazole-5-carboxylate

Product 1

HCID 2077555-Thiazolecarboxylic acid, 2-ethyl-Yield 83.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-ethylthiazole-5-carboxylate (400 mg, 2.159 mmol) in MeOH (10 mL) is added 1N NaOH (6 mL, 6 mmol) After stirring at room temperature for 18 hours, the crude is concentrated under reduced pressure to remove MeOH. The crude is diluted with EtOAc, the organic layer is washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 2-ethylthiazole-5-carboxylic acid (282.4 mg). HPLC retention time=0.78 minutes (condition D); MS (m+3)=160.4; 1H NMR (400 MHz, CD3OD) δ ppm 1.40 (t, J=7.6 Hz, 3 H) 3.07 (q, J=7.6 Hz, 2 H) 5.08 (br. s., 1 H) 8.20 (s, 1 H).

Workup

  1. concentrationthe crude is concentrated under reduced pressure
  2. customto remove MeOH
  3. additionThe crude is diluted with EtOAc
  4. washthe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-317ebed3836e4379821d0959b5f0027f
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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