1-(Chloromethyl)-4-(phenylthio)benzene

518.0 g of 4-phenylmercaptobenzyl alcohol, 147 ml of pyridine and 2444 ml of dichloromethane were charged into a 5000 mL reaction flask at room temperature (25 ° C.), and the mixture was cooled in ice water to control the temperatureThionyl chloride was added dropwise at 20-24 ° C and the mixture was stirred at room temperature (25 ° C) for 2 hours. TLC (n-hexane: ethyl acetate = 10: 1) was carried out to the end of the reaction. Washed with water, neutralized with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure (pressure 1720 Pa, temperature 25 ° C) to dryness. Methylene chloride was recovered to obtain 548.0 g of brownish red oil with a yield of 97.7percent and HPLC purity of 99.66 percent. (Frozen to about -10 curable).The 4-benzoquinone benzyl alcohol, pyridine, and dichloromethane were put into the reaction flask at room temperature (25 °C), ice-cooled and cooled at 20-24 °C, thionyl chloride was added dropwise, and the mixture was stirred at 25° C for 2 hours. Thin layer detection (n-hexane:ethyl acetate=10:1) to the end of the reaction, washing with water to neutrality, drying the dichloromethane layer over anhydrous magnesium sulfate, filtering, and depressurizing the filtrate (pressure 1720 Pa, temperature 25 °C) To dryness, the methylene chloride was recovered to give a brown-red oil (frozen to about -10 °C or so). See Table 4 for details710 g of sodium hydroxide, 511.2 g of 1- (2, 4-dichlorophenyl) -2-imidazole ethanol, 1136 ml of water, 5680 ml of toluene and 56.8 g of tetrabutylammonium bromide were placed in a room temperature (25 ° C.) 10L reaction flask, stirring was warmed to 58 ° C, a solution of In 1000ml of three necked flask equipped with a stirrer, thermometer, dropping funnel added 25.6g of 1-(2, 4-dichlorophenyl)-2-imidazol-ethanol (0.1mol) , 120ml tetrahydrofuran, 40ml water, 6g (0. 15mol) of sodium hydroxide , 1.2g PEG-400 and slowly warmed to reflux. While stirring added drop wise 4-Phenylthio-benzylchloride 30g (0. 12 mol 95percent), completion of the addition in approximately 30min and stirring at constant temperature for 4h, then the reaction was cooled, added 400ml of Diethyl ether, separatedaqueous layer, then aqueous layer was extracted with diethyl ether (200ml X2), combined the organic layer, washed with water , dried over anhydrous sodiumsulfate, filtrate , at the room temperature in filtrate liquid slowy & dropwise added 10ml concentrated nitric acid, precipitate solid, suction filtered, washed with diethyl ether, recrystallized using 95percent of ethanol to obtain white solid 37.3g, yield 82.1percent. mp 136-138oC.At room temperature (25 °C) Sodium hydroxide, 1- (2, 4-dichlorophenyl) -2-imidazol ethanol, water, toluene, tetrabutylammonium bromide administered into the reaction flask, heated with stirring to 58 °C 4-phenyl benzyl benzyl chloride in toluene was added dropwise, and the addition was completed in 1.5 h. Insulation reaction 12h, layers were separated aqueous layer was discarded, and the organic layer was washed with a saturated aqueous sodium chloride solution, washed with water, the toluene layer was dried over anhydrous magnesium sulfate, filtered and the filtrate under reduced pressure (pressure of 1330 Pa, a temperature of 55 °C) and concentrated to dryness recovered toluene to give an oil, was added a mixed solvent (ethyl acetate: toluene = 1: 1), added 20percent nitric acid in ethyl acetate solution at room temperature (25 °C) was stirred for 3h crystallization, filtration, water washing, collecting The filter cake was dried under normal pressure at 40 °C to give a pale yellow solid710 g of sodium hydroxide, 511.2 g of 1-(2, 4-dichlorophenyl)-2-imidazoleethanol, 1136 ml of water, 5680 ml of toluene and 56.8 of tetrabutylammonium bromide at room temperature (25 °C). g, put into a 10L reaction bottle, stir and heat to 58 °C, A toluene solution of 4-phenylhydrazinobenzyl chloride (554.1 g - 1130 ml) was added dropwise, and the dropwise addition was completed over 1.5 hours. The reaction was carried out at 60 °C for 12 hours, the layers were separated, the aqueous layer was discarded, and the organic layer was washed three times with a saturated aqueous solution of sodium chloride (250 ml X 1 + 200 ml Chi 2).The mixture was washed twice with water (200 ml X 2 ), dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to dryness under reduced pressure (1330 Pa, temperature 55 °C) to yield toluene to give an oil of 1250.5 g. Toluene = 1:1) 5680ml, Further, and then 20percent of nitric acid was added 1136 ml of anethyl ester solution was stirred at 25 °C for 3 hours, filtered, washed with water, and the filter cake was collected and dried at 40 °C to give 738 g of pale yellow solid. The yield was 71.4percent, and the HPLC purity was 99.84percent.

Molecular Weight:234.74
XLogP3:4.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:234.0269992
Monoisotopic Mass:234.0269992
Topological Polar Surface Area:25.3
Heavy Atom Count:15
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes