Hexane → HCID 54026803, compound

HRID 849042Notes

Reaction equation

HRID 849042 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.[CH3:19][N:20]1[C:24]([CH3:25])=[C:23]([N:26]=[C:27]=[S:28])[C:22]([CH3:29])=[N:21]1>C1COCC1>[CH3:19][N:20]1[C:24]([CH3:25])=[C:23]([NH:26][C:27]([N:15]2[C:16]3[C:12](=[CH:11][C:10]([Cl:9])=[CH:18][CH:17]=3)[CH:13]=[CH:14]2)=[S:28])[C:22]([CH3:29])=[N:21]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 82127Potassium hydrideHCID 871105-ChloroindoleHCID 3263055ST50844634

Product 1

HCID 54026803HCID 54026803, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred slurry of hexane washed potassium hydride (0.423 g, 10.6 mmol) in 50 mL of dry THF was treated portionwise with 5-chloroindole (1.6 g, 10.6 mmol). The mixture was stirred until a clear solution was obtained. A solution of (1,3,5-trimethyl-pyrazol-4-yl)-isothiocyanate (1.8 g, 10.6 mmol) of step A in 5 mL THF was slowly added and stirring was continued for 1 hour. 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 foam was triturated with Et2O-hexane overnight to provide 2.0 g of the title compound as a tan solid, m.p. 165-166° C. (59% 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 foam was triturated with Et2O-hexane overnight

Sources & evidence

ORD record
ord-42f5055a81aa490683d2af002fde7a34
Source dataset
uspto-grants-2000_01
Patent number
US06011053

Reaction notes

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