N-Benzylideneaniline → Diphenylacetylene

HRID 2253869Notes

Reaction equation

HRID 2253869 reaction equation
CC(C)([O-])C.[K+].[C:7]1([CH2:13]N2C=NC=N2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:19]1([CH:25]=NC2C=CC=CC=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[C:7]1([C:13]#[C:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 10858N-BenzylideneanilineHCID 224581-(Phenylmethyl)-1H-1,2,4-triazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 10390DiphenylacetyleneYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To potassium t-butoxide (5.6 g, 50 mmol) in DMF (40 mL) at 75° C. was added N-(phenylmethyl)-1H-1,2,4-triazole (1.59 g, 10 mmol) and N-(phenylmethylene)benzenamine (1.81 g, 10 mmol) dissolved in DMF (10 mL). After 30 minutes the solution is poured into ice-cold water (150 mL), extracted with CHCl3 (3×50 mL) and chromatographed (PE). Diphenylacetylene was obtained in 11% yield.

Workup

  1. extractionextracted with CHCl3 (3×50 mL)
  2. customchromatographed (PE)

Sources & evidence

ORD record
ord-2279ee5b710a4c34a9ae49a35d5ddb91
Source dataset
uspto-grants-1993_08
Patent number
US05233046

Reaction notes

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