N1-(4-Chlorophenyl)-1,2-benzenediamine

NIn the hydrogenation reactor, 100 g of N- (4-chlorophenyl) -2-nitro-1-aniline and 200 g of DMF were charged, After nitrogen replacement, Put 10 grams of nickel metal catalyst.Turn on stirringWarming to 60 degrees, Hydrogen gas to 3 kg pressure.Continuous access to hydrogen at 60 to 70 degrees, Until it no longer absorbs hydrogen, HPLC-controlled reaction process.When the condensate intermediate disappears, The reaction reached the end.Nitrogen replacement reaction system, Nickel catalyst was removed by hot filtration.The resulting filtrate was concentrated under reduced pressure to give about 100 g of DMF, Add 200 grams of deionized water, After slowly cooling to 20 degrees crystallization.The solid was isolated by filtration, After the solid was washed with appropriate amount of deionized water, Then cold toluene washing, drying.Finally, 81 g of crude N- (4-chlorophenyl) -1, 2-phenylenediamine was obtained, Yield 92percentPurity greater than 98percentColor is gray brown.EXAMPLE 3 STR8 21.9 parts of 4'-chloro-2-amino-diphenylamine and 35.6 parts of the monoazo dye obtained from diazotised 1-aminonaphthalene-6-sulfonic acid and salicylaldehyde are suspended in 250 parts by volume of ethylene glycol. To this suspension are then added 16.9 parts of cobalt sulfaheptahydrate (corresponding to 3.54 parts of cobalt). The reaction mixture is heated to 85-90 C. while simultaneously raising the pH value of the suspension to 8-9 by addition of 5 N sodium hydroxide solution. The reaction mixture is kept at this temperature, while keeping the pH constant with 5 N sodium hydroxide solution, until the metallisation is complete. The cobalt-containing dye is precipitated by addition of sodium chloride solution, then collected by filtration and dried.80g of 2-amino-4'-chlorodiphenylamine, 500ml of methanol, and 500ml of 30% iron trichloride solution were added into the flask, and heated upto 60-70 C for 3-4 hours, after the reaction , cooled to 0 C and filtered to give cake, which was dried to obtain a crude Clofazimine (Compound 4, which contains about 20% of compound 2). Dried filter cake was added to the flask, 50g of isopropylamine, 500ml of dioxane, was added, and the reaction was refluxed for 12-14 hours, the reaction was completed, the reaction solution was concentrated to dryness, a mixed solution of 500 ml of methanol and 50 ml of dichloromethane was added to the flask and the mixture was refluxed for 2 hours, and crystallized at 0 C for 2 hours, and filtered to obtain a filter cake, which was a crude product of Clofazimine (Compound 1), 61 g, yield 70.4. %, purity 99.0%. The resulting filtered mother liquor was concentrated to dryness, 50 ml of methanol was added to reflux, and the mixture was cooled and crystallized, filtered, and dried to obtain 12 g of the title compound, Compound 2, yield 15.0%, purity 92.5%.Take 30 g of the clofazimine condensate isomer, 150 ml of 5 mol/L sulfuric acid, 150 ml of methanol, 150 ml of dioxane were added, the temperature was raised to 40 C, and the reaction was carried out for 72 hours, the reaction was concentrated to a liquid free flow and 150 ml of toluene was added, it was neutralized with saturated sodium carbonate, the layers were separated, and the aqueous phase was further extracted with 150 ml of toluene, and the toluene layer was combined, the organic phase was concentrated to about 150 ml of toluene remaining, warmed to 80 C, stirred for 1h, cooled and crystallized , the mixture was stirred at room temperature and filtered to give 27.0 g of 2-amino-4'-chlorodiphenylamine, yield 88.8%, purity 98.5%.

Molecular Weight:218.68
XLogP3:3.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:218.0610761
Monoisotopic Mass:218.0610761
Topological Polar Surface Area:38
Heavy Atom Count:15
Complexity:190
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes