O-Xylene → HCID 23094081, compound

Reaction equation

N1C=CC=CC=1NC1C=CC=CC=1C(N[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)=O.[N+:24]([C:27]1[CH:39]=[CH:38][CH:37]=[CH:36][C:28]=1[NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)([O-])=O.[C:40]1(C)C(C)=CC=CC=1>>[N:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[N:29]1[C:28]2[CH:36]=[CH:37][CH:38]=[CH:39][C:27]=2[N:24]=[C:40]1[C:13]1[CH:14]=[CH:15][C:16]([Br:19])=[CH:17][CH:18]=1

Participants

Reactant 3

HCID 7237O-Xylene

HCID 23094082HCID 23094082, compound

HCID 59785875N-(2-Nitrophenyl)pyridin-2-amine

Product 1

HCID 23094081HCID 23094081, compoundYield 67%

Procedure

Suspending 5.5 g (15.0 mmol) of 2-(2-pyridylamino)-4′-bromobenzanilide obtained in the above step (2) into 60 milliliter of xylene, and adding 0.86 g (4.5 mmol) of p-toluenesulfonic acid 1 hydrate, the resultant solution was azeotropically dehydrated while refluxing with heating for 8 hours. The reacted solution was cooled down to room temperature, and the solvent was removed by distillation. Dissolving the resultant solid into ethyl acetate, and after sequentially washing with water, with 10% potassium carbonate aqueous solution and with saturated solution of sodium chloride, it was dried with sulfuric anhydride magnesium, followed by removing the solvent by distillation under reduced pressure, 3.5 g of 1-(2-pyridyl)-2-(4-bromophenyl)-1H-benzimidazole was obtained (yield: 67%).