2-Methylindole → HCID 9926898, compound

HRID 849043Notes

Reaction equation

HRID 849043 reaction equation
[H-].[K+].[CH3:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[H][H].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:25])=[C:20]([N:22]=[C:23]=[S:24])[CH:21]=1>C1COCC1.CCOCC.CCCCCC>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:25])=[C:20]([NH:22][C:23]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[C:4]2[CH3:3])=[S:24])[CH:21]=1

Participants

8

Reactant 4

HCID 72242-MethylindoleHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 82127Potassium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 9926898HCID 9926898, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

A stirred slurry of hexane washed potassium hydride (1.51 g, 38 mmol) in 10 mL of dry THF was treated dropwise with a solution of 2-methylindole (5.0 g, 38 mmol) in 30 mL THF. The mixture was stirred until hydrogen evolution ceased. To the dark red solution was slowly added 5-chloro-2-methylphenylisothiocyanate (7 g, 38 mmol) 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 to give 11.5 g of rose colored solids. The solids were dissolved in Et2O and clarified with Norite-A. Hexane was added to the filtered solution and the precipitate was collected and dried to give 7.0 of the title compound as a light yellow solid, m.p. 121-122° C. (53% of theory).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between EtOAc and 1N HCl
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give 11.5 g of rose
  7. customthe precipitate was collected
  8. customdried

Sources & evidence

ORD record
ord-081b771128ef45a5b50f7155d4324532
Source dataset
uspto-grants-2000_01
Patent number
US06011053

Reaction notes

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