2-[4-(Aminomethyl)phenyl]benzonitrile → 4'-[(3-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)methyl]biphenyl-2-carbonitrile

HRID 36180Notes

Reaction equation

HRID 36180 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=1)#[N:2].[C:17]([NH:22][N:23]=[C:24](OCC)[CH2:25][CH2:26][CH2:27][CH3:28])(OCC)=[O:18]>C(O)C>[CH2:25]([C:24]1[N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]#[N:2])=[CH:14][CH:13]=2)[C:17](=[O:18])[NH:22][N:23]=1)[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 13933412-[4-(Aminomethyl)phenyl]benzonitrileHCID 53752329Ethyl valerate carbethoxyhydrazone

Product 1

HCID 149510524'-[(3-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)methyl]biphenyl-2-carbonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 400 mg (1.923 mmole) of [(2'-cyanobiphenyl-4-yl)methyl]amine, 457 mg (2.12 mmole) of ethyl valerimidate carbethoxyhydrazone (from Example 2, Step A), and 7 mL of ethanol was stirred under N2 in an oil bath at 50° C. for 3 hours and then at 80° C. for 2 days. The mixture was cooled and concentrated. The residue, re-concentrated from toluene, was flash chromatographed over silica gel (gradient elution with 1.5-5% methanol in CH2Cl2) to give 591 mg (93%) of desired product, homogeneous in TLC (90:10 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 333 (M+1)+.

Workup

  1. waitat 80° C. for 2 days
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. concentrationThe residue, re-concentrated from toluene
  5. customchromatographed over silica gel (gradient elution with 1.5-5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-583298ebf36447bfa4a5925b8a8453ee
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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