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

HRID 1448912Notes

Reaction equation

HRID 1448912 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) π 2.23-2.60 (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-ac219839d7ac461d9bcdce11ea71a5b2
Source dataset
uspto-grants-1980_02
Patent number
US04188325

Reaction notes

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