Benzaldehyde → 5,6-dimethyl-2-styryl-1H-1,3-benzimidazole

HRID 50932Notes

Reaction equation

HRID 50932 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([CH3:12])[C:9]([CH3:11])=[CH:10][C:4]=2[N:3]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCOCC>[CH3:11][C:9]1[C:8]([CH3:12])=[CH:7][C:5]2[NH:6][C:2](/[CH:1]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:3][C:4]=2[CH:10]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 768912,5,6-Trimethylbenzimidazole

Product 1

HCID 59172955,6-dimethyl-2-styryl-1H-1,3-benzimidazoleYield 13%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2,5,6-trimethyl-1H-benzimidazole (1.5 g, 9.4 mmol) and benzaldehyde (5.0 g, 47 mmol) was heated to 200° C. for 3 h in a sealed tube. The reaction mixture was cooled to room temperature and then ether (50 ml) was added. The precipitated solids were collected by filtration to afford 300 mg (13%) of (E)-5,6-dimethyl-2-styryl-1H-benzimidazole as light yellow solids. 1H-NMR (CDCl3) δ: 8.39-8.33 (1H, m), 7.58-7.47 (2H, m), 7.24-7.16 (5H, m), 6.82 (1H, d, J=16.5 Hz), 5.20 (1H, br.s), 2.13 (6H, s).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe precipitated solids were collected by filtration

Sources & evidence

ORD record
ord-a22c60fc4b1b4987aebea6ac5f302563
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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