N-Methylaniline → HCID 178419229, compound

HRID 648110Notes

Reaction equation

HRID 648110 reaction equation
[B:1](Cl)(Cl)[Cl:2].[CH3:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl-:2].[Cl-:2].[CH3:5][N:6]([BH2:1])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 25135Boron Trichloride

Product 1

HCID 178419229HCID 178419229, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of boron trichloride (14.77 g) in toluene (60 ml), a solution of methylaniline (13.5 g) in toluene (30 ml) is added dropwise at -20° C. with stirring. A solution of triethylamine (12.8 g) in toluene (20 ml) is added to the above mixture, which is stirred at room temperature overnight. The precipitate is filtered under nitrogen atmosphere and washed with toluene. The filtrate and washings are combined, evaporated under reduced pressure to remove the toluene, and the residue is distilled to give N-methylanilinoborane dichloride (10.5 g) as an oil distilling at 60° to 65° C./3 mm Hg. [Niedenzu, J. Am. Chem. Soc., 81, 5553 (1959)].

Workup

  1. stirringis stirred at room temperature overnight
  2. filtrationThe precipitate is filtered under nitrogen atmosphere
  3. washwashed with toluene
  4. customevaporated under reduced pressure
  5. customto remove the toluene
  6. distillationthe residue is distilled

Sources & evidence

ORD record
ord-906c9c219af7420489133cb896b13b51
Source dataset
uspto-grants-1983_10
Patent number
US04410730

Reaction notes

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