Hexane → HCID 9794989, compound

HRID 849040Notes

Reaction equation

HRID 849040 reaction equation
CCCCCC.[H-].[K+].[Cl:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[CH:15][NH:16]2)=[CH:12][CH:11]=1.[CH:19]([N:22]=[C:23]=[S:24])([CH3:21])[CH3:20]>C1COCC1>[CH:19]([NH:22][C:23]([N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]([Cl:9])[CH:18]=2)[CH:14]=[CH:15]1)=[S:24])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 8058HexaneHCID 75263Isopropyl IsothiocyanateHCID 82127Potassium hydrideHCID 871116-Chloroindole

Product 1

HCID 9794989HCID 9794989, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred slurry of hexane washed potassium hydride (0.56 g, 13.9 mmol) in 25 mL of dry THF was treated portionwise with 6-chloroindole (2.0 g, 13.9 mmol). The mixture was heated at reflux until a clear solution was obtained. A solution of isopropyl isothiocyanate (1.4 g, 13.9 mmol) in 5 mL THF was slowly added and stirring was continued for 1 hour. The solvent was evaporated 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 amber solids were recrystallized from EtOH to provide 2.2 g of the title compound as a cream colored solid, m.p. 92-93° C. (63% of theory).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux until a clear solution
  3. customwas obtained
  4. customThe solvent was evaporated
  5. customthe residue partitioned between EtOAc and 1N HCl
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residual amber solids were recrystallized from EtOH

Sources & evidence

ORD record
ord-a3012e399c27431384cabc95c0a3ea52
Source dataset
uspto-grants-2000_01
Patent number
US06011053

Reaction notes

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