1,3-Dimethyl-1,3-dihydro-2H-indole-2-thione → HCID 20351114, compound

HRID 2052577Notes

Reaction equation

HRID 2052577 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH3:11])[C:3]1=[S:12].[Cl:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:13][C:4]1([CH3:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]1=[S:12]

Participants

4

Reactant 2

HCID 261571,3-Dimethyl-1,3-dihydro-2H-indole-2-thioneHCID 31398Chlorosuccinimide

Product 1

HCID 20351114HCID 20351114, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 1-methyl-3-methylthiooxindole (1.07 g, 5.56 mmol) and N-chlorosuccinimide (800 mg, 6.0 mmol) in 75 ml of carbon tetrachloride was stirred at room temperature for 1 hour, filtered, and the filtrate was evaporated to give a residue yielding 3-chloro-1-methyl-3-methylthiooxindole. The residue was dissolved in 20 ml of tetrahydrofuran and rapidly added to a vigorously stirred slurry of red mercuric oxide (1.20 g, 5.56 mmol) and boron trifluoride etherate (790 mg, 5.56 mmol) in 75 mol of 20 percent aqueous tetrahydrofuran. After stirring at room temperature for 1 hour, the reaction mixture was filtered through a Celite pad and the filtrate was extracted with ether. Evaporation of the ether layer gave a residue which was purified by chromatography on silica gel. Elution with methylene chloride gave 1-methylisatin (550 mg, 61%), mp 131°-133°; nmr (CDCl3) τ2.23-2.60 (m, 2H, aromatic H), 2.71-2.90 (m, 2H, aromatic H) and 6.70 (s, 3H, N--CH3).

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated
  3. customto give a residue

Sources & evidence

ORD record
ord-dd63adab1f8d49a5b982d48399997b81
Source dataset
uspto-grants-1980_01
Patent number
US04186132

Reaction notes

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