Hydrochloric Acid → 7-hydroxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3(2H)-one

HRID 846669노트

반응식

HRID 846669 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[S:11])[CH2:5]2.Br[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:19])[C:14](OCC)=[O:15].[OH-].[Na+].Cl>CN(C=O)C.O>[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[C:14](=[O:15])[C:13]([CH3:19])([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[S:11][C:6]3=[CH:5][C:4]=2[CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3778911Ethyl 2-bromo-2-phenylpropanoateHCID 157249681,3-Dihydro-5-hydroxyindol-2-thione

생성물 1

HCID 157249697-hydroxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3(2H)-one수율 82%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution (13 ml) of 1,3-dihydro-5-hydroxyindol-2-thione (1.26 g) and ethyl 2-bromo-2-phenylpropionate (1.88 g) in DMF, an aqueous 2N sodium hydroxide solution (7.3 ml) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with water, made acidic by adding 6N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and a saturated aqueous sodium chloride solution, and was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (diluting solvent: methylene chloride) to give 1.77 g (yield: 81/9 %) of 7-hydroxy-2-methyl-2-phenylthiazolo[3,2-a]indol-3(2H)-one.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, and was dried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (diluting solvent: methylene chloride)

출처 및 근거

ORD 기록
ord-009f39e58caa4affb51503870ce6bcfc
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05137909

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