Toluene → HCID 21940731, compound

HRID 1470793Notes

Reaction equation

HRID 1470793 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[Na+].CO[C:9]1[CH:10]=[C:11](Cl)[CH:12]=[C:13](OC)[CH:14]=1.C1(C)C=CC=CC=1.[CH3:25][NH:26][C:27]1C=C[CH:30]=[CH:29][CH:28]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.F[B-](F)(F)F.C1(P(C2CCCCC2)C2C(OC)=CC=CC=2OC)CCCCC1.C(Cl)Cl>[C:9]1([N:26]([C:27]2[CH:28]=[C:29]([CH3:30])[CH:3]=[C:2]([CH3:5])[CH:1]=2)[CH3:25])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 1140Toluene2×HCID 7515N-MethylanilineHCID 815021-Chloro-3,5-dimethoxybenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 21940731HCID 21940731, compoundYield 88.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 131732731HCID 131732731, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Under the protection of nitrogen, palladium acetate (4.4 mg, 0.02 mmol), dicyclohexyl(2,6-dimethoxyphenyl)phosphine tetrafluoroborate (14.4 mg, 0.03 mmol), sodium tertbutoxide (155.1 mg, 97%, 1.6 mmol), 3,5-dimethoxychlorobenzene (68.8 mg, 0.4 mmol) and 1 mL of toluene were added to the reactor sequentially. The mixture is stirred at room temperature for 4 minutes. N-methylphenyl amine (86.1 mg, 0.8 mmol) and another 1 mL of toluene were added into the reactor. The reactor was heated to 110° C. and the temperature is maintained for 24 hours. After the reactor is cooled, 10 mL of methylene dichloride was used to quench the reaction. Filtration and column chromatography (petroleum: ethyl acetate: triethylamine=100:1:1) afforded 74.5 mg of N-phenyl-N-methyl-3,5-dimethylphenylamine. The yield is 77%.

Workup

  1. temperatureThe reactor was heated to 110° C.
  2. temperaturethe temperature is maintained for 24 hours
  3. temperatureAfter the reactor is cooled
  4. customto quench
  5. customthe reaction
  6. filtrationFiltration and column chromatography (petroleum: ethyl acetate: triethylamine=100:1:1)

Sources & evidence

ORD record
ord-97577e2ab6fe4d6d9314449e5dfb7916
Source dataset
uspto-grants-2015_04
Patent number
US09006491B2

Reaction notes

Loading…