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

HRID 471200Notes

Reaction equation

HRID 471200 reaction equation
O.[OH-].[Li+].[CH2:4]([C:7]1[S:8][CH:9]=[C:10]([C:12]([O:14]CC)=[O:13])[N:11]=1)[CH2:5][CH3:6].Cl>C1COCC1.O>[CH2:4]([C:7]1[S:8][CH:9]=[C:10]([C:12]([OH:14])=[O:13])[N:11]=1)[CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 2036314-Thiazolecarboxylic acid, 2-propyl-, ethyl ester

Product 1

HCID 184357622-Propyl-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (4.4 g) was added to a solution of ethyl 2-propylthiazole-4-carboxylate (example 87, step b) (5.24 g) in a mixture of THF (80 mL) and water (20 mL). The resulting mixture was stirred overnight. The reaction was acidified with concentrated hydrochloric acid and the volatiles evaporated. The resulting aqueous mixture was saturated with sodium chloride and extracted with ethyl acetate (3×100 mL). The combined organic solutions were dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a white solid. Yield 2.5 g.

Workup

  1. customthe volatiles evaporated
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic solutions were dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-768b9782e26548d39e9daa764efc10ec
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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