Thionyl Chloride → HCID 44468395, compound

HRID 1878940Notes

Reaction equation

HRID 1878940 reaction equation
[Cl:1][C:2]1[C:3]([OH:21])=[CH:4][C:5]([OH:20])=[C:6]([C:8](=[N:18][NH2:19])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1.[S:22](Cl)(Cl)=O>>[Cl:1][C:2]1[C:3]([OH:21])=[CH:4][C:5]([OH:20])=[C:6]([C:8]2[N:18]=[N:19][S:22][C:9]=2[C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 136403433HCID 136403433, compound

Product 1

HCID 44468395HCID 44468395, compound

Procedure

1-(5-chloro-2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone hydrazone (2a) (0.1 g, 0.33 mmol) is carefully added to thionyl chloride (1 ml). The reaction mixture is stirred at room temperature for 2 hours. The excess of thionyl chloride is evaporated under reduced pressure, the residue is dissolved in chloroform (10 ml). The organic layer is washed twice with NaHCO3 (sat. aq. 10 ml), then with water (15 ml), dried over Na2SO4, concentrated in vacuo. The residue was purified by dry column chromatography (D. S. Pederson, C. Rosenbohm, (2001) Synthesis, 16, 2431-2434).

Workup

  1. customThe excess of thionyl chloride is evaporated under reduced pressure
  2. dissolutionthe residue is dissolved in chloroform (10 ml)
  3. washThe organic layer is washed twice with NaHCO3 (sat. aq. 10 ml)
  4. dry with materialwith water (15 ml), dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. customby dry
  8. customcolumn chromatography (D. S. Pederson, C. Rosenbohm, (2001) Synthesis, 16, 2431-2434)

Sources & evidence

ORD record
ord-730955f7cdc748afa30fd6df63167dd8
Source dataset
uspto-grants-2012_11
Patent number
US08314132B2

Reaction notes

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