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

HRID 471112Notes

Reaction equation

HRID 471112 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 (0.2 g) was added to a solution of ethyl 2-propylthiazole-4-carboxylate (example 56, step b) (0.24 g) in a mixture of THF (4 mL) and water (1 mL). The resulting suspension was stirred overnight at RT. The reaction was acidified with aqueous HCl solution (2M, 3 mL) and evaporated. The residue was partitioned between brine (5 mL) and ethyl acetate (20 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×20 mL). The combined organic solutions were dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a white solid. Yield 0.17 g.

Workup

  1. customevaporated
  2. customThe residue was partitioned between brine (5 mL) and ethyl acetate (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with ethyl acetate (2×20 mL)
  5. dry with materialThe combined organic solutions were dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0c788b6b5f1245fe97f8abd6481d1c93
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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