Benzaldehyde → Benzenamine, 4,4'-(phenylmethylene)bis[N,N-diethyl-3-methyl-

HRID 1679536Notes

Reaction equation

HRID 1679536 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)[CH3:2].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.S(=O)(=O)(O)O>C(O)CCC>[CH2:11]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([CH:13]([C:7]2[CH:8]=[CH:9][C:4]([N:3]([CH2:11][CH3:12])[CH2:1][CH3:2])=[CH:5][C:6]=2[CH3:10])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([CH3:10])[CH:5]=1)[CH3:12]

Participants

5

Reactant 3

HCID 240Benzaldehyde2×HCID 1118Sulfuric AcidHCID 66679N,N-diethyl-m-toluidine

Product 1

HCID 84752Benzenamine, 4,4'-(phenylmethylene)bis[N,N-diethyl-3-methyl-Yield 70%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Into a 100 milliliter round bottom flask fitted with a mechanical stirrer and a dropping funnel is placed 8.85 grams (0.05 moles) of N,N-diethyl-m-toluidine and 3.0 grams (0.03 moles) of benzaldehyde and 10 milliliters of n-butanol containing 0.75 grams of concentrated sulfuric acid. The flask is flushed with nitrogen to remove air and refluxed for 18 hours with a nitrogen atmosphere. The material is then cooled to room temperature. A sufficient amount of sodium bicarbonate is added in order to neutralize the acid. 10 milliliters of methanol is added whereby a yellowish white precipitation is formed. The yellowish white material is filtered out. The material may then be washed with cold methanol in order to remove the yellow color. The material may be recrystallized from either methanol or ethanol. In order to further purify the material, it may be put through a neutral alumina column. The material is eluted with benzene. The first material to be fractionated off of the column is a clear liquid. This liquid is placed in a rotary evaporator and the solvent is removed. The residue is either a clear liquid or a white solid. The material may be recrystallized using methanol or ethanol. White crystals are obtained. A 70 percent yield based upon the benzaldehyde is obtained. The product is vacuum dried in order to remove the remaining solvent.

Workup

  1. customInto a 100 milliliter round bottom flask fitted with a mechanical stirrer and a dropping funnel
  2. customThe flask is flushed with nitrogen
  3. customto remove air
  4. temperaturerefluxed for 18 hours with a nitrogen atmosphere
  5. additionA sufficient amount of sodium bicarbonate is added in order
  6. addition10 milliliters of methanol is added whereby
  7. customa yellowish white precipitation
  8. customis formed
  9. filtrationThe yellowish white material is filtered out
  10. washThe material may then be washed with cold methanol in order
  11. customto remove the yellow color
  12. customThe material may be recrystallized from either methanol or ethanol
  13. customIn order to further purify the material, it
  14. washThe material is eluted with benzene
  15. customThis liquid is placed in a rotary evaporator
  16. customthe solvent is removed
  17. customThe material may be recrystallized
  18. customWhite crystals are obtained
  19. customis obtained
  20. customdried in order
  21. customto remove the remaining solvent

Sources & evidence

ORD record
ord-f8bf6496af5244d48a9596646fbb7962
Source dataset
uspto-grants-1978_03
Patent number
US04081274

Reaction notes

Loading…