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

HRID 846669ノート

反応式

HRID 846669 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-009f39e58caa4affb51503870ce6bcfc
出典データセット
uspto-grants-1992_08
特許番号
US05137909

反応ノート

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