Aniline → N-[(4-chloro-2-methylphenyl)-methylene]benzeneamine

HRID 986071Notes

Reaction equation

HRID 986071 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:10])[CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.CCOCC>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 27576584-Chloro-2-methylbenzaldehyde

Product 1

HCID 13553333N-[(4-chloro-2-methylphenyl)-methylene]benzeneamineYield 77%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-chloro-2-methylbenzaldehyde (3.5 g, 22.6 mmol) and aniline (2.11 g, 22.6 mmol) in toluene (40 ml) was heated at reflux in a Dean-Stark apparatus for 1 hour. The mixture was cooled and evaporated in vacuo to leave an oily residue. The residue was redissolved in ether, washed with 5% sodium bicarbonate solution. The organic phase was separated, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to afford an oily residue which was purified by distillation via a Kugelrohr apparatus (oven temperature 160° C., 0.5 mm) to provide the title compound (4.0 g, 7.4 mmol, 77%) as a viscous oil; pmr(CDCl3) δ 2.5 (3H, s), 6.3~7.5 (7H, m), 7.95 (H, d), 8.6 (H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux in a Dean-Stark apparatus for 1 hour
  3. temperatureThe mixture was cooled
  4. customevaporated in vacuo
  5. customto leave an oily residue
  6. washwashed with 5% sodium bicarbonate solution
  7. customThe organic phase was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo
  11. customto afford an oily residue which
  12. distillationwas purified by distillation via a Kugelrohr apparatus (oven temperature 160° C., 0.5 mm)

Sources & evidence

ORD record
ord-292a8415cd9645a89abb94670ed0972a
Source dataset
uspto-grants-1987_12
Patent number
US04710513

Reaction notes

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