3,4-Dimethylaniline → HCID 9837228, compound

HRID 324715Notes

Reaction equation

HRID 324715 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.[Cl-].[Ca+2].[Cl-].[Cl-].[Al+3].[Cl-].[Cl-].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([CH3:24])[CH:18]=1>C1C2C(=CC=CC=2)CCC1.C1(C)C=CC=CC=1>[CH3:24][C:19]1[CH:18]=[C:17]([NH:16][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=2)[CH:22]=[CH:21][C:20]=1[CH3:23]

Participants

7

Reactant 4

HCID 72483,4-DimethylanilineHCID 7934m-ToluidineHCID 5284359Calcium ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 9837228HCID 9837228, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8404TetralinSolvent

Procedure

In a 500-ml four-necked flask were charged 56 ml of 1,2,3,4-tetrahydronaphthalene (boiling point: 207° C.) as a solvent and 45.0 g (0.42 mol) of m-toluidine, followed by the addition of 25.6 g (0.23 mol) of anhydrous calcium chloride and 30.8 g (0.23 mol) of anhydrous aluminum chloride under stirring. After stirring at an internal temperature of 100 to 120° C. for 30 minutes under a nitrogen atmosphere, the reaction mixture was added with 50.9 g (0.42 mol) of 3,4-xylidine. The resulting mixture was reacted at an internal temperature of 210 to 220° C. for 3 hours. After cooling, the reaction mixture was added with 126 ml of toluene, followed by charging in 160 g of ice water. The resulting mixture was stirred and then, allowed to stand, whereby a water layer was separated out. The organic layer was washed successively with 150 ml of a 5% aqueous solution of hydrochloric acid, 100 ml of a 5% aqueous solution of sodium bicarbonate and 100 ml of water. From the organic solvent, the distillate at 134 to 135° C. and a vacuum degree of 0.4 to 0.5 Torr was collected, whereby 37.9 g (yield: 42.7%) of the title compound was obtained as a slightly yellow oil. As a result of HPLC. analysis (column: YMC-A-312, detection UV: 280 nm, flow rate: 1.0 ml/min, eluent: acetonitrile/water=8/2), the compound was found to have a purity of 99.3%.

Workup

  1. stirringAfter stirring at an internal temperature of 100 to 120° C. for 30 minutes under a nitrogen atmosphere
  2. customThe resulting mixture was reacted at an internal temperature of 210 to 220° C. for 3 hours
  3. temperatureAfter cooling
  4. stirringThe resulting mixture was stirred
  5. customwhereby a water layer was separated out
  6. washThe organic layer was washed successively with 150 ml of a 5% aqueous solution of hydrochloric acid, 100 ml of a 5% aqueous solution of sodium bicarbonate and 100 ml of water
  7. distillationFrom the organic solvent, the distillate at 134 to 135° C. and a vacuum degree of 0.4 to 0.5 Torr was collected

Sources & evidence

ORD record
ord-2a11009deb764fa0945f64c225db6bf1
Source dataset
uspto-grants-2001_04
Patent number
US06218576B1

Reaction notes

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