N,N'-Dimethylethylenediamine → N-(4-cyanophenyl)-N-(4-(trimethylsilyl)phenyl)acetamide

HRID 522428Notes

Reaction equation

HRID 522428 reaction equation
[CH3:1][Si:2]([CH3:14])([CH3:13])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.Br[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.C1(C)C(C)=CC=CC=1>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([N:9]([C:6]2[CH:5]=[CH:4][C:3]([Si:2]([CH3:13])([CH3:1])[CH3:14])=[CH:8][CH:7]=2)[C:10](=[O:12])[CH3:11])=[CH:17][CH:18]=1)#[N:21]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 12162Benzonitrile, 4-bromo-HCID 605997HCID 605997, compound

Product 1

HCID 58536159N-(4-cyanophenyl)-N-(4-(trimethylsilyl)phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7237O-XyleneSolvent

Procedure

Under a flow of argon, in a 1 L-recovery flask, 27 g of N-(4-(trimethylsilyl)phenyl)acetamide, 30 g of 4-bromobenzonitrile, 6.3 g of copper (I) iodide, 45.6 g of potassium carbonate, and 412 mL of xylene were placed. After stirring, 7.1 mL of N,N′-dimethylethylenediamine was added. The resultant was heated and stirred at reflux for 18 hours.

Workup

  1. temperatureThe resultant was heated
  2. stirringstirred
  3. temperatureat reflux for 18 hours

Sources & evidence

ORD record
ord-7cbec13858e745bbbf8209935a0bd2df
Source dataset
uspto-grants-2016_05
Patent number
US09331285B2

Reaction notes

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