Hydrochloric Acid → 2-Bromo-4-methyl-1,3-thiazole-5-carboxylic acid

HRID 2199199Notes

Reaction equation

HRID 2199199 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([Br:11])=[N:8][C:7]=1[CH3:12])=[O:5])C.O.[OH-].[Li+].Cl>O1CCCC1.O.C(OCC)(=O)C>[Br:11][C:9]1[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH3:12])[N:8]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 28240582-Bromo-4-methyl-1,3-thiazole-5-carboxylic acidYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid ethyl ester (3.0 g, 12 mmol) in tetrahydrofuran (THF, 50 mL) and water (5 mL) was added lithium hydroxide hydrate (1.0 g, 24 mmol). The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was diluted with water and ethyl acetate. The aqueous layer was made acidic to pH 1 with 2 N hydrochloric acid (HCl) and then was extracted with ethyl acetate. The organic extracts were dried over sodium sulfate (Na2SO4), filtered and concentrated to provide product as an orange solid (2.6 g, 98%): mp 152-155° C.; 1H NMR (300 MHz, CDCl3) δ 2.74 (s, 3H); ESIMS m/z 221 (M−1).

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4e901ce0b68041efb7e9f4e541f55eb4
Source dataset
uspto-grants-2016_06
Patent number
US09357780B2

Reaction notes

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