p-Toluidine → Benzenamine, 2-methyl-N-(2-methylphenyl)-

HRID 1282478

Reaction equation

HRID 1282478 reaction equation
O([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.N[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C(C2C=CC=CC=2)=C(P(C2CCCCC2)C2CCCCC2)C)C=CC=CC=1.[Cl-].[NH4+:69]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:12]1([CH3:15])[CH:13]=[CH:14][CH:9]=[CH:10][C:11]=1[NH:69][C:29]1[CH:30]=[CH:25][CH:26]=[CH:27][C:28]=1[CH3:31]

Participants

9

Reactant 6

HCID 7813p-ToluidineHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 5724814-Methylphenyl trifluoromethanesulphonateHCID 2758875Trifluoromethanesulfonate3×HCID 12010824Cy-vBRIDP

Product 1

HCID 136423Benzenamine, 2-methyl-N-(2-methylphenyl)-Yield 65%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Into a reactor were introduced 0.503 g (2.10 mmol) of p-tolyl triflate and 4 mL of dioxane under a nitrogen atmosphere. The triflate was dissolved in the solvent. To this solution were added 0.246 g (2.29 mmol) of p-toluidine, 0.658 g (3.10 mmol) of potassium phosphate, 19.9 mg (2.1 mol % based on the triflate) of tris(dibenzylideneacetone)dipalladium, and 58.7 mg (7.2 mmol % based on the triflate) of the 1,1-diphenyl-2(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 12 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.268 g (65%) of ditolylamine. The results obtained are shown in Table 20.

Workup

  1. customThe resultant reaction mixture
  2. temperaturecooled
  3. extractionthis mixture was extracted with toluene
  4. dry with materialThe extract was dried with anhydrous magnesium sulfate
  5. customThereafter, the solvent was removed under reduced pressure
  6. customThe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-ee5445f5ddd04a17aed2e6d60f2922ab
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Linked notes

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