Ethanol → HCID 15335325, compound

HRID 1449628Notes

Reaction equation

HRID 1449628 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]#[N:17])=[C:7]([C:12]([F:15])([F:14])[F:13])[N:8]2[CH3:11])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[Na].[CH2:23]([OH:25])[CH3:24]>C(Cl)(Cl)(Cl)Cl.C(OCC)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]#[N:17])=[C:7]([C:12]([F:13])([F:14])[F:15])[N:8]2[CH2:11][O:25][CH2:23][CH3:24])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 15335324HCID 15335324, compound

Product 1

HCID 15335325HCID 15335325, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6-chloro-3-cyano-1-methyl-2-(trifluoromethyl)indole (1.08 g, 4.2 mmole) and thionyl chloride (0.68 mL, 8.4 mmole) in carbon tetrachloride is heated at reflux temperature for 18 hours, cooled to room temperature and concentrated in vacuo for 18 hours to remove all volatiles. The residue is dissolved in ethanol and treated with a solution of sodium metal (0.38 g, 16 mmole) in ethanol, stirred or 0.5 hour at room temperature and diluted with diethyl ether. The diluted reaction mixture is washed with water, dried over Na2SO4 and concentrated in vacuo to give a residue. The residue is chromatographed (silica gel/4:1 hexanes: ethyl acetate) to afford the title product as an off-white solid, 0.66 g (52% yield) mp 83°-86° C., identified by IR, 1HNMR, 13CNMR, 19FNMR and mass spectral analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 18 hours
  3. concentrationconcentrated in vacuo for 18 hours
  4. customto remove all volatiles
  5. dissolutionThe residue is dissolved in ethanol
  6. customThe diluted reaction mixture
  7. washis washed with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customto give a residue
  11. customThe residue is chromatographed (silica gel/4:1 hexanes: ethyl acetate)

Sources & evidence

ORD record
ord-0d054580c2ca42d68d2932463c6ab8d4
Source dataset
uspto-grants-1997_02
Patent number
US05599832

Reaction notes

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