Ethylenediamine → 4-[(2-Aminoethyl)amino]benzonitrile

HRID 1249705Notes

Reaction equation

HRID 1249705 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]([NH2:13])[CH2:11][NH2:12].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[NH2:12][CH2:11][CH2:10][NH:13][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 183216654-[(2-Aminoethyl)amino]benzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-fluorobenzonitrile (167 g, 1.38 mol), ethylenediamine (330 g, 5.5 mol) and potassium carbonate (300 g, 2.17 mol) in 2 1 of toluene is refluxed for 6 hours. After cooling to room temperature, the mixture is filtered and rinsed with toluene, and the filtrate is evaporated to give a yellow oil which is crystallized from toluene. The product is filtered off, rinsed with toluene and dried under vacuum at 50° C. to give 200 g of a slightly yellow solid.

Workup

  1. temperatureis refluxed for 6 hours
  2. filtrationthe mixture is filtered
  3. washrinsed with toluene
  4. customthe filtrate is evaporated
  5. customto give a yellow oil which
  6. customis crystallized from toluene
  7. filtrationThe product is filtered off
  8. washrinsed with toluene
  9. customdried under vacuum at 50° C.
  10. customto give 200 g of a slightly yellow solid

Sources & evidence

ORD record
ord-2fce94f3af454f98b266b54212583144
Source dataset
uspto-grants-2002_01
Patent number
US06335337B1

Reaction notes

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