Chlorosuccinimide → HCID 20351111, compound

HRID 2052565Notes

Reaction equation

HRID 2052565 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[S:12])[CH:6]2[CH3:13].[Cl:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:14][C:6]1([CH3:13])[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][C:7]1=[S:12]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 20289274HCID 20289274, compound

Product 1

HCID 20351111HCID 20351111, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 5-methoxy-3-methylthiooxindole (420 mg, 2 mmol) and N-chlorosuccinimide (270 mg, 2 mmol) in carbon tetrachloride (74 ml) was stirred at room temperature for 1 hour. The precipitate was removed by filtration and the filtrate was evaporated to dryness, yielding crude 3-chloro-5-methoxy-3-methylthiooxindole. The residue was dissolved in tetrahydrofuran (10 ml) and added to a vigorously stirred slurry of red mercuric oxide (435 mg, 2 mmol) and boron trifluoride etherate (290 mg, 2 mmol) in aqueous 20 percent tetrahydrofuran (40 ml). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered through a pad of Celite and the filtrate was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography on silica gel to give 5-methoxyisatin (287 mg, 81%), mp 202°-204° (recrystallized from benzene).

Workup

  1. customThe precipitate was removed by filtration
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9dff7414f6a74d11abf73eb5f79d7738
Source dataset
uspto-grants-1980_01
Patent number
US04186132

Reaction notes

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