N-(2-CHLORO-PHENYL)-GUANIDINE synthesis
- Product Name:N-(2-CHLORO-PHENYL)-GUANIDINE
- CAS Number:24067-35-4
- Molecular formula:C7H8ClN3
- Molecular Weight:169.61
Yield:-
Reaction Conditions:
Stage #1: thioureawith copper(ll) sulfate pentahydrate;sodium acetate in dimethyl sulfoxide;N,N-dimethyl-formamide at 20; for 1 h;
Stage #2: o-chloroanilinewith copper(ll) sulfate pentahydrate in dimethyl sulfoxide at 20;
Steps:
3.2. General Procedure for the Synthesis of 2-(N-arylamino)Benzimidazole
General procedure: To a stirred solution of DMSO (2-3 mL), thiourea (1 mmol, 76 mg) was added slowly, followedby the addition of NaOAc (1 mmol, 82 mg) and a copper source (50 mol%) at room temperature.The whole reaction mixture was stirred for 1 h (until a black-colored solution was obtained) at roomtemperature. To this, 2-bromoaniline (2 mmol, 344 mg) was added. After completion of the reaction(monitored by TLC), the reaction mixture was transferred into tubes and the mixture was centrifugedfor 10 min. A black solid was then recovered from the tubes, and to this a clear solution of iodobenzene(1 mmol, 204 mg), K2CO3 (2 mmol, 277 mg), Cu(SO)4.5H2O (20 mol%, 50 mg), and 1,10-phenanthroline(20 mol%, 36 mg) was added slowly in several minutes, and the reaction mixture was then allowedto stir for 18 h at 120 °C. Progress of the reaction was monitored by TLC, using ethyl acetate andhexane (1:4). After completion of the reaction, the reaction mixture was cooled to room temperature.Then, the solution was washed with ethyl acetate (7 mL) and water (3 mL) for 5 times. The organic layerwas evaporated, and the crude reaction mixture was purified on asilica gel (60-120 mesh) column bychromatography to obtain the final product 2-(N-arylamino)benzimidazole, which was characterizedby NMR (1H and 13C), IR, and mass spectral data.
References:
Adil, Syed Farooq;Alduhaish, Osamah;Assal, Mohamed E.;Bollikolla, Hari Babu;Gollapudi, Ravi Kumar;Murthy Boddapati, S. N.;Nurbasha, Sharmila;Siddiqui, Mohammed Rafiq H.;Tamminana, Ramana [Molecules,2020,vol. 25,# 8]
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