Hydrochloric Acid → 2-Bromo-1,3-thiazole-4-carboxylic acid

HRID 1697450Notes

Reaction equation

HRID 1697450 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9]CC)=[O:8])[N:6]=1.[OH-].[Na+].Cl>C(O)C.O>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylate

Product 1

HCID 27632092-Bromo-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

Ethyl 2-bromothiazole-4-carboxylate (600 mg, 2.54 mmol) was suspended in ethanol (15 mL). Sodium hydroxide (7.5 mL, 1 M) was added and the reaction mixture was stirred at 35° C. for 0.5 hours. The reaction mixture was acidified to pH ˜3 with 1 M HCl, then diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL). The organic extracts were combined, washed with brine (100 mL), dried (sodium sulfate), filtered and concentrated to provide the title compound. MS (APCI) m/z=208/210 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with brine (100 mL)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7dc48b2b033242f3b3191c8fe8463f5b
Source dataset
uspto-grants-2012_04
Patent number
US08163916B2

Reaction notes

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