Potassium Carbonate → 4-(4-Butyl-phenylamino)-benzamide

HRID 1354964Notes

Reaction equation

HRID 1354964 reaction equation
C([O-])([O-])=O.[K+].[K+].[NH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1.[CH2:17]([C:21]1[CH:26]=[CH:25][C:24](Cl)=[CH:23][CH:22]=1)[CH2:18][CH2:19][CH3:20]>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].CC1C=CC(C(C2C=CC(C)=CC=2)C(=O)C(C)C)=CC=1.CC(O)(C)C>[CH2:17]([C:21]1[CH:26]=[CH:25][C:24]([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=2)=[CH:23][CH:22]=1)[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 760794-AminobenzamideHCID 524314Benzene, 1-butyl-4-chloro-

Product 1

HCID 211061294-(4-Butyl-phenylamino)-benzamideYield 88%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 120407443-Methyl-1,1-bis(4-methylphenyl)-2-butanoneCatalystHCID 6386tert-ButanolSolvent2×

Conditions

Temperature
110 °C

Procedure

An oven-dried resealable Schlenk flask was evacuated and backfilled with argon. The flask was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol, 1 mol % Pd), Ligand 1 (9.4 mg, 0.02 mmol, 2 mol %), ground K2CO3 (193 mg, 1.4 mmol), and 4-amino-benzamide (163 mg, 1.2 mmol). The flask was evacuated and backfilled with argon (3×) and then capped with a rubber septum. To the flask was added t-BuOH (1.5 mL), 4-n-butyl-chlorobenzene (168 mg, 1.0 mmol) and t-BuOH (0.5 mL). The septum was replaced with a Teflon screwcap, the flask was sealed, and the mixture was heated to 110° C. with stirring until the starting aryl chloride was consumed by GC analysis (19 h). The reaction was cooled to room temperature, diluted with ethyl acetate, filtered through Celite, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel (eluting with EtOAc/hexanes, 8:2) to give the desired product as a white solid (235 mg, 88%).

Workup

  1. customAn oven-dried resealable Schlenk flask was evacuated
  2. customThe flask was evacuated
  3. customcapped with a rubber septum
  4. customthe flask was sealed
  5. customwas consumed by GC analysis (19 h)
  6. temperatureThe reaction was cooled to room temperature
  7. additiondiluted with ethyl acetate
  8. filtrationfiltered through Celite
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by column chromatography on silica gel (eluting with EtOAc/hexanes, 8:2)

Sources & evidence

ORD record
ord-58e79b1e6f374465bf7caf9d533bd043
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

Loading…