Hydrochloric Acid → 4-Tert-butyl-2-[5-(2-carboxymethylphenylmethoxy)benzofuran-2-yl]thiazole hydrochloride

HRID 487707Notes

Reaction equation

HRID 487707 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27]C#N)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[ClH:32].[C:33](=[O:36])([O-])[OH:34].[Na+]>COCCOCCO.[OH-].[Na+]>[ClH:32].[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][C:33]([OH:34])=[O:36])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 19092790HCID 19092790, compound

Product 1

HCID 190927474-Tert-butyl-2-[5-(2-carboxymethylphenylmethoxy)benzofuran-2-yl]thiazole hydrochloride

Reagents, catalysts & solvents 2

HCID 8134Diethylene Glycol Monomethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 4-tert-butyl-2-[5-(2-cyanomethylphenylmethoxy)benzofuran-2-yl]thiazole (0.5 g) and 40% aqueous potassium hydroxide (10 ml) in diethylene glycol monomethyl ether (10 ml) was heated at 110-120° C. for 1.5 hours. After being cooled, the resulting solution was poured into ice-water, acidified with diluted aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give crude residue. The residue was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate (4:1). The fractions containing object compound were combined and concentrated to give an oil. The oil was dissolved in aqueous sodium hydrogen carbonate and washed with ethyl acetate. The ethyl acetate layer was concentrated under reduced pressure to give an oil, which was dissolved in aqueous sodium hydroxide and adjusted to pH 1 with diluted aqueous hydrochloric acid. The resulting precipitates were collected by filtration and washed with water to give 4-tert-butyl-2-[5-(2 -carboxymethylphenylmethoxy)benzofuran-2-yl]thiazole hydrochloride (5.00 g).

Workup

  1. temperatureAfter being cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crude residue
  7. washeluted with a mixture of n-hexane and ethyl acetate (4:1)
  8. additionThe fractions containing object compound
  9. concentrationconcentrated
  10. customto give an oil
  11. washwashed with ethyl acetate
  12. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  13. customto give an oil, which
  14. customThe resulting precipitates
  15. filtrationwere collected by filtration
  16. washwashed with water

Sources & evidence

ORD record
ord-1f44e2dd72aa4bcca2321ab8a49f86c8
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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