N-Methylethylenediamine → HCID 54805899, compound
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:48]1[C:53]([CH3:54])=[CH:52][C:51]([CH3:55])=[CH:50][C:49]=1[CH3:56].[CH3:57][NH:58][CH2:59][CH2:60][NH2:61].CC(C)([O-])C.[Na+]>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].C1(C)C=CC=CC=1>[CH3:57][NH:58][CH2:59][CH2:60][NH:61][C:48]1[C:53]([CH3:54])=[CH:52][C:51]([CH3:55])=[CH:50][C:49]=1[CH3:56]Participants
Procedure
In a 100 mL round-bottom flask tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (110 mg, 0.120 mmol) and (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene ((±)-BINAP) (230 mg, 0.37 mmol) were added to 25 mL toluene and stirred for 20 minutes. Next, 2-bromomesitylene (2.45 g, 12.3 mmol), N-methylethylenediamine (1.01 g, 13.6 mmol) and sodium t-butoxide (NaOtBu) (3.56 g, 37 mmol) were added along with 25 mL toluene. This was stirred for 72 hours at 80° C. The flask was then removed from heat, cooled to room temperature and diluted with 20 mL diethyl ether. The solution was then washed with 5×30 mL water and 3×15 mL brine, and dried over magnesium sulfate. After filtering and vacuum removal of solvent, a dark red oil was recovered and used without further purification.
Workup
- stirringThis was stirred for 72 hours at 80° C
- customThe flask was then removed
- temperaturefrom heat
- additiondiluted with 20 mL diethyl ether
- washThe solution was then washed with 5×30 mL water and 3×15 mL brine
- dry with materialdried over magnesium sulfate
- filtrationAfter filtering
- customvacuum removal of solvent
- customa dark red oil was recovered
- customused without further purification
Sources & evidence
- ORD record
- ord-72c99d56e7294b7086d02a2c5153cc1b
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09024034B2
Reaction notes
Loading…