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

HRID 487707노트

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HRID 487707 반응식
[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]

참가 물질

7

반응물 4

HCID 313Hydrochloric Acid2회HCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 19092790HCID 19092790, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 8134Diethylene Glycol Monomethyl Ether용매HCID 14798Sodium Hydroxide용매

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온도
115 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1f44e2dd72aa4bcca2321ab8a49f86c8
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05296495

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