O-Phenylenediamine → 2-(1,3-benzodioxol-5-yl)-1H-benzimidazole

HRID 366852Notes

Reaction equation

HRID 366852 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.[C:12]1([NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18]>[N+](C1C=CC=CC=1)([O-])=O>[O:11]1[C:3]2[CH:2]=[CH:1][C:6]([C:7]3[NH:19][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N:18]=3)=[CH:5][C:4]=2[O:9][CH2:10]1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 8438Piperonal

Product 1

HCID 2429622-(1,3-benzodioxol-5-yl)-1H-benzimidazoleYield 49%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A solution of 50 g (0.34 mol) of piperonal and 37 g (0.34 mol) of phenylenediamine in 0.3 L of nitrobenzene was stirred under reflux for 12 hours. The resulting mixture was concentrated in vacuo. The solid residue was collected via filtration, and rinsed with ether to give 39.6 g (49%) of desired material as an off-white solid: 1H NMR (CDCl3) δ 5.96 (s, 2H), 6.79 (d, J=8.5 Hz, 1H), 7.17-7.30 (m, 2H), 7.50-7.65 (m, 4H), 8.80-9.40 (br s, 1H).

Workup

  1. temperatureunder reflux for 12 hours
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. filtrationThe solid residue was collected via filtration
  4. washrinsed with ether

Sources & evidence

ORD record
ord-1083927ef4f84be38a5e87d42ce324ea
Source dataset
uspto-grants-2000_10
Patent number
US06130333

Reaction notes

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