Hydrochloric Acid → 2-Butyl-4-thiazolecarboxylic acid

HRID 471175Notes

Reaction equation

HRID 471175 reaction equation
[OH-].[Li+].[CH2:3]([C:7]1[S:8][CH:9]=[C:10]([C:12]([O:14]CC)=[O:13])[N:11]=1)[CH2:4][CH2:5][CH3:6].Cl>C1COCC1.O>[CH2:3]([C:7]1[S:8][CH:9]=[C:10]([C:12]([OH:14])=[O:13])[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67292599Ethyl 2-butyl-1,3-thiazole-4-carboxylate

Product 1

HCID 140500762-Butyl-4-thiazolecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (5.00 g) was added to a stirred mixture of ethyl 2-butylthiazole-4-carboxylate (example 78, step f) (6.50 g) in THF (80 mL) and water (20 mL). After 16 h, concentrated hydrochloric acid (10 mL) was added and the solution concentrated to ˜40 mL. The reaction mixture was partitioned between ethyl acetate and brine. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulphate, filtered and evaporated in vacuo to give the subtitled compound as an off white solid. Yield 4.6 g.

Workup

  1. concentrationthe solution concentrated to ˜40 mL
  2. customThe reaction mixture was partitioned between ethyl acetate and brine
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-17e638a012aa4b4fb6b0b39125795901
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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