3,5-Dichlorobenzaldehyde → HCID 67330016, compound

HRID 1672365Notes

Reaction equation

HRID 1672365 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH2:6])[CH3:2].[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[CH:14]=O>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[CH:14]=[N:6][CH2:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 357463,5-DichlorobenzaldehydeHCID 695242,2-Diethoxyethylamine

Product 1

HCID 67330016HCID 67330016, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
114 °C

Procedure

The 2,2-Diethoxy-ethylamine (1852.5 g; 1.00 equiv; 13.63 moles), 3,5-dichloro-benzaldehyde (2453 g; 1.00 equiv; 13.60 moles), and Toluene (12 L) is charged to a 22 L flask equipped with a Dean Stark trap, condenser, nitrogen inlet, overhead stirring, and thermocouple. The light yellow reaction is warmed to reflux. Solvent begins distilling at 88° C. A total of ˜650 mL distillate (˜240 mL of water) is collected. The temperature is increased to 114° C. during the distillation. NMR after 2 hr at reflux shows the product. The heat is shut off after 2.5 hr. The solution is gravity filtered into a carboy through fluted filter paper to remove a few particulates (including a small section of glass tubing, which is most likely from the 3,5-dichloro-benzaldehyde). The filtered solution is concentrated using Buchi flask with the water bath set at 45° C. Once the solvent stops coming over, the temperature is increased to 70° C. with full vacuum and held for ˜1.5 hr to remove any residual toluene. The weight of (3,5-Dichloro-benzylidene)-(2,2-diethoxy-ethyl)-amine is 4059.3 g (102.9% of theory). Mass Spectrum (LCMS) m/z=291.2) (M+H+)

Workup

  1. customequipped with a Dean Stark trap, condenser, nitrogen inlet
  2. customThe light yellow reaction
  3. temperatureis warmed to reflux
  4. distillationSolvent begins distilling at 88° C
  5. distillationA total of ˜650 mL distillate (˜240 mL of water) is collected
  6. temperatureNMR after 2 hr at reflux
  7. filtrationfiltered into a carboy
  8. filtrationthrough fluted filter paper
  9. customto remove a few particulates (
  10. concentrationThe filtered solution is concentrated
  11. customset at 45° C
  12. temperatureis increased to 70° C. with full vacuum
  13. waitheld for ˜1.5 hr
  14. customto remove any residual toluene

Sources & evidence

ORD record
ord-ebdf624535824504a06758597944d1da
Source dataset
uspto-grants-2011_08
Patent number
US07998977B2

Reaction notes

Loading…