2,6-Dichloro-N-phenylbenzenamine

Light brown powder

The compound II (272 g, 0.92 mol), toluene (800 g, 8.7 mol) was dried in a four-necked flask, heated to 90 ° C, and sodium hydroxide was added three times with stirring, and 14.8 g (0.37 mol) was added.The reaction was refluxed for 3 hours and then cooled to below 80 ° C. 184 mL of distilled water was added to the reaction flask and the temperature was raised to 90 ° C. The mixture was stirred for 1 hour. The reaction solution was transferred to a separatory funnel.To the reaction solution was further added 46 mL of water and 28 mL of hydrochloric acid, and the reaction solution was transferred to a distillation flask, distilled under reduced pressure, and toluene was distilled off to give 203.4 g of a pale yellow solid (Compound III: N- (2, 6- Chlorophenyl) aniline), yield 93percent.EXAMPLE 22 EXAMPLE 23 The procedure of Example 22 was repeated except that 40 g (0.38 mole) of sodium carbonate was used and that the reaction temperature was kept at 95° C. to give 66.3 g of N-phenyl-2, 6-dichloroaniline (yield: 87percent, purity: 95.1percent).Preparation of 2, 6-dichlorodiphenylamine A mixture of 996 g of 2, 6-dichlorophenoxyacetic acid ethyl ester, 500 ml of aniline and 400 ml of n-butanol is preheated to 100° C. in a distillation apparatus. 400 ml of 5.5N sodium methylate are run in over a period of 30 minutes during which a flow of distillate is maintained by the exothermic heat of the reaction. After addition of the sodium methylate, stirring is continued for 15 minutes at 100° C. with continued removal of distillate. 1 l of water is then added and solvent is distilled off down to the sump temperature of 90° C. Phase separation takes place at 60° C. The solvent is drawn off in a vacuum and the product is crystallized from 1l of 90percent i-propanol. The product is separated by suction filtration at 0° C. and washed with dilute i-propanol. Yield: 727 g=76.5percent of the theoretical yield with exploitation of the mother liquor to an extent of 82percent of the theoretical.(1) 2, 6-dichloroaniline and 1, 4-dioxane (600 ml) were added to a reaction flask, stirred and dissolved, and then chlorobenzene, potassium phosphate (261.929 g, 1.234 mol) and a catalyst (0.031) were added. Mol), Stirring to 130 C, heat preservation reaction for 20 h;The molar ratio of the chlorobenzene to the 2, 6-dichloroaniline is 1.5:1;The catalyst is nano cuprous iodide particles, Nano cuprous iodide is prepared according to the method described in the literature (The Journal of Organic Chemistry 2011, 76, 2296-2300).(2) The reaction mixture obtained in the step (1) is cooled to 80 C, then filtered with diatomaceous earth, the filtrate is collected, the filter cake is washed with hot water at 50 C, the washing liquid is collected, the filtrate and the washing liquid are combined, and the water is distilled off under reduced pressure. Chlorobenzene and 1, 4-dioxane were obtained as a crude product; the crude product was dissolved in dichloromethane, and then a water layer was added, and the solvent was distilled off in dichloromethane to give 2, 6-dichlorodiphenylamine.; The contents of Example 31 were substantially the same as those of Example 24, except that the molar ratio of the chlorobenzene to 2, 6-dichloroaniline was 4:1; and the catalyst was nano-copper oxideEXAMPLE 22 A 1 l glass reactor was charged with 100 g (0.32 mole) of N-phenyl-2, 2, 6, 6-tetrachlorocyclohexaneimine obtained in and 500 g of chlorobenzene, and the mixture was heated in an oil bath with stirring. While keeping the reaction temperature at 100 C., the reaction was continued for 5 hours. After the reaction was completed, the reaction mixture was cooled to 25 C., and washed with 300 g of a 10% aqueous solution of sodium hydroxide. Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure to give 64.7 g of Exemplified Compound 11 (0091)

Diclofenac intermediate.

Molecular Weight:238.11
XLogP3:4.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:237.0112047
Monoisotopic Mass:237.0112047
Topological Polar Surface Area:12
Heavy Atom Count:15
Complexity:182
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes