Sodium Hydroxide → 2-Chloro-5-(2-methyl-1,3-thiazol-4-yl)benzoic acid

HRID 1988391Notes

Reaction equation

HRID 1988391 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[C:12]([CH3:15])[S:13][CH:14]=2)[CH:7]=[CH:6][C:5]=1[Cl:16].[OH-].[Na+]>C(O)(C)(C)C>[Cl:16][C:5]1[CH:6]=[CH:7][C:8]([C:10]2[N:11]=[C:12]([CH3:15])[S:13][CH:14]=2)=[CH:9][C:4]=1[C:3]([OH:17])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 588181942-Chloro-5-(2-methyl-thiazol-4-yl)-benzoic acid methyl ester

Product 1

HCID 184386562-Chloro-5-(2-methyl-1,3-thiazol-4-yl)benzoic acidYield 69%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 2-chloro-5-(2-methyl-thiazol-4-yl)-benzoic acid methyl ester (10 mg, 0.04 mmol) and sodium hydroxide (80 μL, 1M aqueous, 0.08 mmol) in tert-butanol (1 mL) was stirred at room temperature for 3 d. The mixture was concentrated to dryness in vacuo, dissolved in water (5 mL), acidified to pH 6 (1M HCl) and extracted with ethyl acetate. The combined organic layers were washed with water, and brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound (7 mg).

Workup

  1. concentrationThe mixture was concentrated to dryness in vacuo
  2. dissolutiondissolved in water (5 mL)
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water, and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3823e27843974f118c7eedad789552a1
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

Loading…