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

HRID 456893Notes

Reaction equation

HRID 456893 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 pH6 (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-2698b2d07ea9447785decb2c10e934c3
Source dataset
uspto-grants-2007_03
Patent number
US07186742B2

Reaction notes

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