N-Benzylideneaniline → Diphenylacetylene

HRID 2253868Notes

Reaction equation

HRID 2253868 reaction equation
CC(C)([O-])C.[K+].[C:7]1([CH2:13]N2C3C=CC=CC=3N=C2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:23]1([CH:29]=NC2C=CC=CC=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[C:23]1([C:29]#[C:13][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10858N-BenzylideneanilineHCID 5633471-Benzyl-1H-benzimidazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 10390DiphenylacetyleneYield 73%

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-benzimidazole (2.08 g, 10 mmol) and N-(phenylmethylene)benzenamine (1.81 g, 10 mmol) dissolved in DMF (10 mL). After 5 hours the solution is poured into ice-cold water (150 mL), extracted with CHCl3 (3×50 mL) and chromatographed (PE). Diphenylacetylene was obtained in 73% yield.

Workup

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

Sources & evidence

ORD record
ord-c25f7c966ce5422c93c253e65a6fa027
Source dataset
uspto-grants-1993_08
Patent number
US05233046

Reaction notes

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