Ammonia → 3,5-Dimethylbenzonitrile

HRID 984692Notes

Reaction equation

HRID 984692 reaction equation
[C-]#N.[K+].C[NH:5][CH2:6][CH2:7]NC.BrC1[CH:12]=[C:13]([CH3:18])[CH:14]=[C:15]([CH3:17])[CH:16]=1.CCCCCCCCCCCC.N>C(OCC)(=O)C.[Cu]I.C1(C)C=CC=CC=1>[CH3:18][C:13]1[CH:12]=[C:7]([CH:16]=[C:15]([CH3:17])[CH:14]=1)[C:6]#[N:5]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 8182DodecaneHCID 9032Potassium CyanideHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 897183,5-DimethylbenzonitrileYield 15%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
110 °C

Procedure

A Schlenk tube was charged with CuI (19.5 mg, 0.102 mmol, 20 mol %), KCN (78 mg, 1.20 mmol), evacuated, backfilled with Ar. N,N′-Dimethylethylenediamine (21.5 μL, 0.202 mmol, 20 mol %), 5-bromo-m-xylene (136 μL, 1.00 mmol), and toluene (1.0 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 24 h. Dodecane (internal GC standard, 230 μL), ethyl acetate (2 mL), and 30% aq ammonia (1 mL) were added. A 0.1 mL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide a 15% yield of 3,5-dimethylbenzonitrile.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve

Sources & evidence

ORD record
ord-a04f30ff7576452387f28e1e0f9d1c5b
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

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