Chlorosuccinimide → HCID 20351113, compound

HRID 2052574Notes

Reaction equation

HRID 2052574 reaction equation
[CH3:1][S:2][CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N+:12]([O-:14])=[O:13])[NH:5][C:4]1=[O:15].[Cl:16]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:16][C:3]1([S:2][CH3:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N+:12]([O-:14])=[O:13])[NH:5][C:4]1=[O:15]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 12351492HCID 12351492, compound

Product 1

HCID 20351113HCID 20351113, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methylthio-4-nitrooxindole (1.58 g, 7 mmol) and N-chlorosuccinimide (1.20 g, 9 mmol) in 100 ml of methylene chloride was stirred at room temperature for 48 hours. The solvent was removed in vacuo, yielding crude 3-chloro-3-methylthio-4-nitrooxindole. The residue was dissolved in 25 ml of tetrahydrofuran and added rapidly in a vigorously stirred slurry of red mercuric oxide (1.52 g, 7 mmol) and boron trifluoride etherate (1.00 g, 7 mmol) in 100 ml of 50 percent aqueous tetrahydrofuran. After stirring for 3 hours, the solution was filtered through a Celite pad which was then washed with copious amounts of chloroform. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. The residue was chromatographed on silica gel. Elution with chloroform-ethanol (9:1) gave 4-nitroisatin (535 mg, 40%), mp 248°-250° (dec) (recrystallized from ethanol); ir (KBr) 3200 (NH), 1750 (C=O), 1710 (C=O), 1520 (NO2) and 1350 cm-1 (NO2); nmr (DMSO-d6)τ-1.30 (1H, b s, NH), 2.20-2.80 (m, 3H, aryl H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-36518b5ea0b5468a90ce5df15df33d93
Source dataset
uspto-grants-1980_01
Patent number
US04186132

Reaction notes

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