Benzamide → N-(3,5-dimethylphenyl)benzamide

HRID 1883328Notes

Reaction equation

HRID 1883328 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C@@H]1(N)CCCC[C@H]1N.Br[C:25]1[CH:26]=[C:27]([CH3:32])[CH:28]=[C:29]([CH3:31])[CH:30]=1>[Cu]I.O1CCOCC1>[CH3:32][C:27]1[CH:26]=[C:25]([NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:30]=[C:29]([CH3:31])[CH:28]=1

Participants

7

Reactant 4

HCID 2331BenzamideHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 2306655N-(3,5-dimethylphenyl)benzamideYield 90.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

An oven-dried resealable Schlenk tube was charged with CuI (4.0 mg, 0.0210 mmol, 1.0 mol %), benzamide (300 mg, 2.48 mmol), K2CO3 (600 mg, 4.38 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (26 μL, 0.216 mmol, 11 mol %), 5-bromo-m-xylene (280 μL, 2.06 mmol) and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 23 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 3:1; 15 mL fractions). Fractions 10-15 provided 419 mg (90% yield) of the product as white crystals. 1H NMR (400 MHz, CDCl3): δ 7.92−7.85 (m, 3H), 7.59-7.75 (m, 3H), 7.31 (s, 2H), 6.82 (s, 1H), 2.34 (s, 6H). 13C NMR (100 MHz, CDCl3): δ 165.6, 138.7, 137.7, 135.1, 131.7, 128.7, 126.9, 126.3, 117.9, 21.3. IR (neat, cm−1): 3300, 1649,1614, 1547.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed
  3. temperatureThe resulting suspension was cooled to room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 3:1; 15 mL fractions)

Sources & evidence

ORD record
ord-73d380306df3426d8f7cdac50185031b
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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