Carbon Tetrachloride → 1,5-Diacetyl-3-[chloro-(pyrazin-2-yl)-methylidene]-2-indolinone

HRID 347994Notes

Reaction equation

HRID 347994 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)[C:6](=[C:16]([C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)O)[C:5]1=[O:24])(=[O:3])[CH3:2].C(Cl)(Cl)(Cl)[Cl:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)[C:6](=[C:16]([Cl:26])[C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)[C:5]1=[O:24])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 178465971HCID 178465971, compound

Product 1

HCID 689932081,5-Diacetyl-3-[chloro-(pyrazin-2-yl)-methylidene]-2-indolinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.2 g (3.7 mmol) 1,5-diacetyl-3-[pyrazin-2-yl-hydroxy-methylidene]-2-indolinone (Ex. V.23) are dissolved in 50 ml dioxane and refluxed with 2 ml carbon tetrachloride and 2 g triphenylphosphine for 5 h. Then the mixture is left to cool and evaporated down. The residue is chromatographed through a silica gel column with methylene chloride/methanol 25:1, the corresponding fractions are combined and concentrated by rotary evaporation.

Workup

  1. waitThen the mixture is left
  2. temperatureto cool
  3. customevaporated down
  4. customThe residue is chromatographed through a silica gel column with methylene chloride/methanol 25:1
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-88df44742d5549788c6ebd00d09fe491
Source dataset
uspto-grants-2007_02
Patent number
US07176231B2

Reaction notes

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