Hexane → HCID 10220629, compound

HRID 849039Notes

Reaction equation

HRID 849039 reaction equation
CCCCCC.[H-].[K+].[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2.[CH:19]([N:22]=[C:23]=[S:24])([CH3:21])[CH3:20]>C1COCC1>[CH:19]([NH:22][C:23]([N:15]1[C:16]2[C:12](=[CH:11][C:10]([Cl:9])=[CH:18][CH:17]=2)[CH:13]=[CH:14]1)=[S:24])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 8058HexaneHCID 75263Isopropyl IsothiocyanateHCID 82127Potassium hydrideHCID 871105-Chloroindole

Product 1

HCID 10220629HCID 10220629, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred slurry of hexane washed potassium hydride (0.87 g, 21.8 mmol) in 50 mL of dry THF was treated portionwise with 5-chloroindole (3.3 g, 21.8 mmol). The mixture was heated at reflux until a clear solution was obtained. A solution of isopropyl isothiocyanate (2.2 g, 21.8 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 amber solids were recrystallized from EtOH to provide 3.4 g of the title compound as a tan solid, m.p. 135° C. (62% 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 amber solids were recrystallized from EtOH

Sources & evidence

ORD record
ord-44711cd51e484742add16973a7556dd7
Source dataset
uspto-grants-2000_01
Patent number
US06011053

Reaction notes

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