Chlorosuccinimide → HCID 20351125, compound

HRID 1448898Notes

Reaction equation

HRID 1448898 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[S:11].[Cl:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:12][C:2]1([CH3:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[S:11]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 14708632HCID 14708632, compound

Product 1

HCID 20351125HCID 20351125, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 3-methylthiooxindole (1.70 g, 0.0095 mol) and N-chlorosuccinimide (1.34 g, 0.01 mol) in 100 ml of carbon tetrachloride was stirred at room temperature for 1 hour, the precipitate of succinimide was removed by filtration, and the filtrate was evaporated, yielding crude 3-chloro-3-methylthiooxindole. The residue, which was thus obtained, was dissolved in a minimum of tetrahydrofuran and added to a vigorously stirred slurry of red mercuric oxide powder (2.17 g, 0.01 mol) and boron trifluoride etherate (1.43 g, 0.01 mol) in 20 percent aqueous tetrahydrofuran (70 ml). After stirring at room temperature for 1 hour, 200 ml of ether was added, the reaction mixture was filtered through a pad of Celite and the organic phase of the filtrate was separated, dried over anhydrous magnesium sulfate, filtered, and this filtrate was evaporated to give isatin (1.07 g, 78%), mp 200°-202° after recrystallization from benzene.

Workup

  1. customthe precipitate of succinimide was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a0cbf0f45a0449e9b90c6827d477e6d0
Source dataset
uspto-grants-1980_02
Patent number
US04188325

Reaction notes

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