Sodium Hydroxide → 4-(2-Methoxyphenyl)-thiazole-5-carboxylic acid

HRID 1776158Notes

Reaction equation

HRID 1776158 reaction equation
C([O:3][C:4]([C:6]1[S:10][CH:9]=[N:8][C:7]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:7]1[N:8]=[CH:9][S:10][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 670764344-(2-Methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 580160524-(2-Methoxyphenyl)-thiazole-5-carboxylic acidYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the crude 4-(2-methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester (0.88 g) in 95% ethanol (20 ml) was added sodium hydroxide (0.67 g, 16.75 mmol) and the resulting mixture was stirred at room temperature for 5 hours. After acidification with 3N HCl and concentration under vacuum, the remaining residue was taken up with water, and extracted with ethyl acetate (3×50 ml). The combined organics were dried over Na2SO4 and evaporated under reduced pressure to afford the title compound as a yellow solid (0.77 g, 3.28 mmol, a 41% yield). m.p.: 170-172° C.; 1H NMR (200 MHz, DMSO) δ 3.72 (s, 3H, OCH3), 6.99-7.12 (m, 2H, Ar), 7.35-7.46 (m, 2H, Ar), 9.26 (s, 1H, 2-CH).

Workup

  1. concentrationAfter acidification with 3N HCl and concentration under vacuum
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-05fa23ee36fd4e79908a617b893caa36
Source dataset
uspto-grants-2016_02
Patent number
US09265769B2

Reaction notes

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