Water → HCID 68511623, compound

HRID 1512993Notes

Reaction equation

HRID 1512993 reaction equation
[C:1]1([C:7](O)([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][C:12]1[C:13]([N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])=[CH:14][C:15]([SH:20])=[C:16]([O:18][CH3:19])[CH:17]=1.O>ClCCCl.[I-].[Zn+2].[I-]>[Cl:11][C:12]1[C:13]([N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])=[CH:14][C:15]([S:20][C:7]([CH3:9])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])=[C:16]([O:18][CH3:19])[CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 120532-Phenyl-2-propanolHCID 59310058HCID 59310058, compound

Product 1

HCID 68511623HCID 68511623, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 2-phenyl-2-propanol (0.45 g) in 1,2-dichloroethane (5 mL) were added zinc iodide (0.53 g) and a solution of 5-chloro-4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-mercaptoanisole (1 g) in 1,2-dichloroethane (5 mL) successively, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1) to give 5-chloro-4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-(1-methyl-1-phenylethylthio)anisole (1.32 g). This material was dissolved in tetrahydrofuran (20 mL). To the solution was added hydrazine monohydrate (0.73 mL), and the mixture was heated at reflux for 2 hours. The reaction mixture was cooled to room temperature, and the insoluble material was removed by filtration. To the filtrate were added water and ethyl acetate, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1) to give the title compound (0.74 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-4685e0c52c7d4af2a1f1616a826ceff8
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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