Cyanogen Bromide → [(3-Ethylphenyl)amino]carbonitrile

HRID 1069169Notes

Reaction equation

HRID 1069169 reaction equation
[N:1]#[C:2]Br.[CH2:4]([C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9])[CH3:5]>CCOCC>[CH2:4]([C:6]1[CH:7]=[C:8]([NH:9][C:2]#[N:1])[CH:10]=[CH:11][CH:12]=1)[CH3:5]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 114753-Ethylaniline

Product 1

HCID 10012043[(3-Ethylphenyl)amino]carbonitrileYield 96.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of cyanogen bromide (3.31 g, 31.26 mmol) in Et2O (25 ml) was added slowly to a stirred solution of m-ethylaniline (6.06 g, 50 mmol) in Et2O (50 ml) and continued stirring at room temperature for 6 hours. A white precipitate of m-ethylaniline hydrobromide (4.46 g) was filtered off, and the filtrate was washed with H2O (2×20 ml). Evaporation of ether layer afforded the title compound (3.85 g, 96.5%) as a thick liquid.

Workup

  1. filtrationA white precipitate of m-ethylaniline hydrobromide (4.46 g) was filtered off
  2. washthe filtrate was washed with H2O (2×20 ml)
  3. customEvaporation of ether layer

Sources & evidence

ORD record
ord-9109bf362e0e4b3fa611fd10a9d0cdfc
Source dataset
uspto-grants-2001_06
Patent number
US06251948B1

Reaction notes

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