Sodium Hydroxide → 2-Bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylic acid

HRID 2282289Notes

Reaction equation

HRID 2282289 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:15]([O:17]CC)=[O:16])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[N:6]=1.[OH-].[Na+]>C1COCC1.O>[Br:1][C:2]1[S:3][C:4]([C:15]([OH:17])=[O:16])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[N:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58095245Ethyl 2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 580948542-Bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Ethyl 2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylate (4.05 g, 10.6 mmol) in THF (50 mL) and water (20 mL) was added solution of sodium hydroxide in water (1.0M, 31.9 mL, 31.9 mmol). The solution was stirred at room temperature for 16 hours. The reaction was quenched by the addition of aqueous HCl solution (1N, 38 mL), and then extracted five times with ethyl acetate. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give white solid which was dried overnight and then used directly in the next step (3.74 g, 99%). LCMS: (AA) ES+, 354. 1H NMR (400 MHz, d4-Methanol) δ: 7.57-7.55 (m, 1H), 7.41-7.39 (m, 2H).

Workup

  1. customThe reaction was quenched by the addition of aqueous HCl solution (1N, 38 mL)
  2. extractionextracted five times with ethyl acetate
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give white solid which
  8. customwas dried overnight

Sources & evidence

ORD record
ord-892f0eab6b934b4990d189cb81997a0f
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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