Sodium Hydroxide → 5-(4-Fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acid

HRID 1671676Notes

Reaction equation

HRID 1671676 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:17])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:4].[OH-].[Na+]>C1COCC1.CO.O>[F:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]2[S:8][C:7]([CH3:17])=[N:6][C:5]=2[C:3]([OH:4])=[O:2])=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53271155Methyl 5-(4-fluorophenyl)-2-methylthiazole-4-carboxylate

Product 1

HCID 223241255-(4-Fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acidYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carboxylic acid methyl ester (15 g) in a mixture of THF (60 mL) and MeOH (20 mL) was added a solution of sodium hydroxide (2.63 g) in water (60 mL). The reaction mixture was stirred at RT for 30 min. The reaction mixture was then concentrated in vacuo, and the residue was dissolved with water (100 mL) and concentrated again in vacuo. The residue was dissolved in water (250 mL), cooled to 0° C. with a ice-bath. Then was added a solution of conc.HCl (37%)(7.72 g) in water (7.72 g) and stirred at 0° C. for 15 min. The resulting precipitate was filtered off, washed with water and dried in high vacuum pump. to give the title compound as a white solid (13.16 g, 93%).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe residue was dissolved with water (100 mL)
  3. concentrationconcentrated again in vacuo
  4. dissolutionThe residue was dissolved in water (250 mL)
  5. temperaturecooled to 0° C. with a ice-bath
  6. additionThen was added a solution of conc
  7. stirringHCl (37%)(7.72 g) in water (7.72 g) and stirred at 0° C. for 15 min
  8. filtrationThe resulting precipitate was filtered off
  9. washwashed with water
  10. customdried in high vacuum pump

Sources & evidence

ORD record
ord-b759008bfd3e41559b0136de4da3ba0d
Source dataset
uspto-grants-2011_08
Patent number
US07994336B2

Reaction notes

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