HCID 12282158, compound → HCID 178509632, compound
Reaction equation
[NH2:1][CH:2]([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[CH:3]([NH2:11])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.Cl.[Cl:21][C:22]1[CH:32]=[CH:31][C:25]([C:26](=N)OCC)=[CH:24][CH:23]=1>C(O)C>[Cl:21][C:22]1[CH:32]=[CH:31][C:25]([C:26]2[NH:1][CH:2]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[CH:3]([C:4]3[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=3)[N:11]=2)=[CH:24][CH:23]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-[1,2-diamino-2-(4-chloro-phenyl)-ethyl]-benzonitrile (81 mg, 0.298 mmol) and ethyl 4-chloro-benzimidate hydrochloride (55 mg, 0.249 mmol) in ethanol (5 mL) was heated at 72° C. for 5 h. The solvent was removed, and the residue was taken in methylene chloride (10 mL). The reaction mixture was washed with 1 N sodium hydroxide solution (1 mL) and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 0.5% methanol in methylene chloride yielded 4-[2,5-bis-(4-chloro-phenyl)-4,5-dihydro-3H-imidazol-4-yl]-benzonitrile (62 mg, 76%). HR-MS (EI, m/z) calculated for C22H15N3Cl2 (M+) 391.0643, observed 391.0648.