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

HRID 1689345Notes

Reaction equation

HRID 1689345 reaction equation
O.[OH-].[Li+].[CH:4]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([O:14]CC)=[O:13])[N:11]=2)[CH2:6][CH2:5]1.Cl>C1COCC1.O>[CH:4]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([OH:14])=[O:13])[N:11]=2)[CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 18771956Ethyl 2-cyclopropylthiazole-4-carboxylate

Product 1

HCID 187718162-Cyclopropyl-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (0.13 g) was added to a solution of ethyl 2-cyclopropylthiazole-4-carboxylate (example 57, step b) (0.15 g) in a mixture of THF (8 mL) and water (2 mL) and the resulting mixture was stirred overnight. The reaction was acidified with aqueous HCl (2M, 3 mL) and the solvent evaporated. The residue was partitioned between brine (20 mL) and ethyl acetate (30 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×30 mL). The combined organic solutions were dried over sodium sulphate, filtered and evaporated to give the subtitled compound as an off white solid. Yield 0.12 g.

Workup

  1. customthe solvent evaporated
  2. customThe residue was partitioned between brine (20 mL) and ethyl acetate (30 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with ethyl acetate (2×30 mL)
  5. dry with materialThe combined organic solutions were dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8712b452cde94a63be28296685632f9a
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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