Chlorosuccinimide → HCID 20351110, compound

HRID 1448901Notes

Reaction equation

HRID 1448901 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[S:11])[CH:5]2[CH3:12].[Cl:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:13][C:5]1([CH3:12])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[NH:7][C:6]1=[S:11]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 20289281HCID 20289281, compound

Product 1

HCID 20351110HCID 20351110, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 5-chloro-3-methylthiooxindole (1.35 g, 6.3 mmol) and N-chlorosuccinimide (950 mg, 7 mmol) in carbon tetrachloride (100 ml) was refluxed for 1 hour, cooled, and the precipitate was removed by filtration. The filtrate was concentrated to dryness, yielding crude 3,5-dichloro-3-methylthiooxindole. The residue was dissolved in 25 ml of tetrahydrofuran and added rapidly to a vigorously stirred slurry of red mercuric oxide (1.37 g, 6.3 mmol) and boron trifluoride etherate (900 mg, 6.3 mmol) in 100 ml of 20 percent aqueous tetrahydrofuran. After stirring for 3 hours, the solution was filtered through a pad of Celite and the filtrate was extracted with chloroform. The chloroform extracts were dried over anhydrous magnesium sulfate, filtered and the filtrates were concentrated to give a red solid which was chromatographed on silica gel with chloroform as the eluent. There was obtained 5-chloroisatin (850 mg, 75%), mp 248°-251° (recrystallized from ethanol).

Workup

  1. temperaturecooled
  2. customthe precipitate was removed by filtration
  3. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-3dfbbb922e104424989965b09cc2fed1
Source dataset
uspto-grants-1980_02
Patent number
US04188325

Reaction notes

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