2,3-Dimethylindole → N-(5-Chloro-2-methylphenyl)-2,3-dimethyl-1H-indole-1-carbothioic acid amide

HRID 849044Notes

Reaction equation

HRID 849044 reaction equation
CCCCCC.[H-].[K+].[CH3:9][C:10]1[NH:11][C:12]2[C:17]([C:18]=1[CH3:19])=[CH:16][CH:15]=[CH:14][CH:13]=2.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([CH3:30])=[C:25]([N:27]=[C:28]=[S:29])[CH:26]=1>C1COCC1>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([CH3:30])=[C:25]([NH:27][C:28]([N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]([CH3:19])=[C:10]2[CH3:9])=[S:29])[CH:26]=1

Participants

6

Reactant 4

HCID 70532,3-DimethylindoleHCID 8058HexaneHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 82127Potassium hydride

Product 1

HCID 9840417N-(5-Chloro-2-methylphenyl)-2,3-dimethyl-1H-indole-1-carbothioic acid amideYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A stirred slurry of hexane washed potassium hydride (1.38 g, 34.5 mmol) in 10 mL of dry THF was treated dropwise with a solution of 2,3-dimethylindole (5.0 g, 34.5 mmol) in 30 mL THF. The mixture was stirred until a clear solution was obtained. A solution of 5-chloro-2-methylphenylisothiocyanate (6.3 g, 34.5 mmol) in 5 mL THF was slowly added and stirring was continued for 16 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between EtOAc and 1N HCl. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residual solid was triturated with Et2O-hexane overnight to provide 7.5 g of the title compound as a light yellow solid, m.p. 115° C. (67% of theory).

Workup

  1. customwas obtained
  2. stirringstirring
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between EtOAc and 1N HCl
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residual solid was triturated with Et2O-hexane overnight

Sources & evidence

ORD record
ord-1fca7f3b25e04f4ab33035f2ed1ba31e
Source dataset
uspto-grants-2000_01
Patent number
US06011053

Reaction notes

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