Ethanimidic acid, 2,2,2-trichloro-, methyl ester

clear colorless to pale yellow liquid

4-Nitrobenzene-1, 2-diamine 1a (19.33g, 126mmol) was suspended in 200mL of glacial acetic acid, (i) Methyl 2, 2, 2-trichloroacetimidate (480 muL, 3.86 mmol) was added dropwise to a cooled solution of 4-chloro-benzene-1, 2-diamine (500 mg, 3.51 mmol) in acetic acid (20 mL). At the end of the addition (10 min), the reaction mixture was kept at room temperature for 1 h. The reaction mixture was extracted with CH2Cl2, washed with water, dried with anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to provide 5-chloro-2-trichloromethyl-1H-benzimidazole (805 mg, 85%). LRMS (ESI) m/z 269 [M + H]+.24. 55 mmol of PHENYLENEDIAMINE 1a-k, 1M, In were dissolved in 50 ml of acetic acid, AND 27 MMOL of methy 2, 2, 2-TRICHFOROACETIMIDATE 2 WERE added at 0C over the course of 0.5 hour under an N2 atmosphere. When the addition was complete, the reaction mixture was slowly warmed to room temperature and stirred at this temperature for 2 hours. The reaction mixture was poured into ice-water, and the resulting precipitate was filtered off with suction, washed with a little water and dried at 40C under reduced pressure. 3a: R = 5-Cl ; brown solid, yield : 82%At 0 C, 6.3 g (35.9 mmol, 1.1 eq.) of methyl2, 2, 2-trichloroethaneimidoate were added dropwise to a solution of 5.0 g (32.7mmol) of 4-nitrobenzene-1, 2-diamine in 150 ml of glacial acetic acid. Thereaction mixture was stirred at RT for 3 h and then added to 400 ml of water, and 300 ml of ethyl acetate were added. After phase separation, the aqueousphase was extracted twice with ethyl acetate. The combined organic phases werewashed twice with in each case 130 ml of saturated aqueous sodium bicarbonatesolution and once with saturated aqueous sodium chloride solution, dried(sodium sulphate), filtered and concentrated under reduced pressure and dried.The crude product was triturated with pentane and left to stand overnight. Thesolid was then filtered off, washed with pentane and dried under reducedpressure. Yield: 10.1 g (purity 77%, 85% of theory)

Molecular Weight:176.42
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:174.935847
Monoisotopic Mass:174.935847
Topological Polar Surface Area:33.1
Heavy Atom Count:8
Complexity:97.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes