Stannous chloride dihydrate → HCID 53686295, compound

HRID 1164973Notes

Reaction equation

HRID 1164973 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[C:16](=[O:25])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:2].O.O.[Sn](Cl)Cl>C(O)C>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][N:3]([CH2:26][CH3:27])[CH2:1][CH3:2])=[C:8]([C:16](=[O:25])[CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 54387892HCID 54387892, compound

Product 1

HCID 53686295HCID 53686295, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5.00 g (13.6 mmol) of 1-[2-[2-(diethylamino)ethoxy]-5-nitrophenyl]-3-phenyl-2-propen-1-one in 50 mL of ethanol add 9.20 g (40.8 mmol) of tin(II) chloride dihydrate and heat the mixture to reflux with stirring for two hours. After cooling remove the solvent in vacuo. Add water and adjust the pH to 12 with potassium hydroxide. Add ethyl acetate and filter the mixture through celite. Separate the layers of the filtrate and extract the aqueous layer twice with ethyl acetate. Wash the combined organic layers with water, saturated sodium chloride solution, and dry over anhydrous sodium sulfate. Remove the solvent in vacuD to provide the title compound.

Workup

  1. temperatureheat the mixture
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. customremove the solvent in vacuo
  5. filtrationAdd ethyl acetate and filter the mixture through celite
  6. customSeparate the layers of the filtrate
  7. extractionextract the aqueous layer twice with ethyl acetate
  8. washWash the combined organic layers with water, saturated sodium chloride solution
  9. dry with materialdry over anhydrous sodium sulfate
  10. customRemove the solvent in vacuD

Sources & evidence

ORD record
ord-2e32be9137dd47cfb9e1a7a3054db2e8
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

Loading…