Benzaldehyde → 2,4-Dimethoxy-N-(phenylmethylene)benzenemethanamine

HRID 371228Notes

Reaction equation

HRID 371228 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH:13](=[N:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=1[O:2][CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 138550362,4-Dimethoxy-N-(phenylmethylene)benzenemethanamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

12.0 g of 2,4-dimethoxybenzylamine hydrochloride is added to 100 ml of 1N sodium hydroxide solution and the mixture is extracted with 125 ml of ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and stripped of solvent to give 10.2 g of 2,4-dimethoxybenzylamine as an oil. This amine is dissolved in 150 ml of benzene; 6.47 g of benzaldehyde and 0.6 g of p-toluenesulfonic acid monohydrate are added. The mixture is heated under reflux removing water with a Dean-Stark separator and in two hours the calculated amount of water (1.1 ml) separates out. The mixture is cooled to room temperature. Upon further cooling the benzene solution deposits some precipitate. Benzene is removed under reduced pressure and 60 ml of petroleum ether is added to the residue. An oily layer separates out with more precipitate. Benzene (10 ml) is added to make the layers homogeneous and the remaining precipitate is filtered. The filtrate is stripped of solvent to give 14.2 g of the title compound as an oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux
  3. customremoving water with a Dean-Stark separator
  4. temperatureUpon further cooling the benzene solution
  5. customBenzene is removed under reduced pressure and 60 ml of petroleum ether
  6. additionis added to the residue
  7. additionBenzene (10 ml) is added
  8. filtrationthe remaining precipitate is filtered

Sources & evidence

ORD record
ord-4d12b0b3d1974de3942c8f11105faf3f
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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