Stannous Chloride → HCID 70188090, compound

HRID 2269477Notes

Reaction equation

HRID 2269477 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=2)[NH:10][C@@H:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH3:12])=[CH:5][CH:4]=1.[Sn](Cl)Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([NH:10][C@@H:11]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)[CH3:12])[C:20]2[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 70189308HCID 70189308, compound

Product 1

HCID 70188090HCID 70188090, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.72 g of N-[(4-methoxyphenyl)-(3-nitrophenyl)methyl]-N-[(R)-1-p-tolylethyl]amine [prepared as described in step (a) above] were dissolved in 150 ml of ethanol. Tin (II) chloride (15.6 g) was added to the resulting solution, which was then heated under reflux for 3 hours. The reaction mixture was allowed to cool, and the ethanol was distilled off. The residue was dissolved in ethyl acetate. The organic solution was washed with a 1N aqueous solution of sodium hydroxide and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The yellow oil thus obtained was purified by chromatography through a silica gel column using an 8:1 by volume mixture of toluene and tetrahydrofuran as eluant, to obtain 1.43 g and 0.78 g of isomer A and isomer B of the title compound, respectively, each as a pale yellow oil.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. distillationthe ethanol was distilled off
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washThe organic solution was washed with a 1N aqueous solution of sodium hydroxide
  7. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe yellow oil thus obtained
  11. customwas purified by chromatography through a silica gel column
  12. additionby volume mixture of toluene and tetrahydrofuran as eluant

Sources & evidence

ORD record
ord-041ade8ffc74415984cebe63fe978462
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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