Hydrochloric Acid → HCID 15724969, compound

HRID 846669Notes

Reaction equation

HRID 846669 reaction equation
[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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3778911Ethyl 2-bromo-2-phenylpropanoateHCID 15724968HCID 15724968, compound

Product 1

HCID 15724969HCID 15724969, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-009f39e58caa4affb51503870ce6bcfc
Source dataset
uspto-grants-1992_08
Patent number
US05137909

Reaction notes

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