Structure of 59363-13-2
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CAS No. : | 59363-13-2 |
Formula : | C10H12Cl2O |
M.W : | 219.11 |
SMILES Code : | OC(CCl)CCC1=CC=C(Cl)C=C1 |
MDL No. : | MFCD12407177 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.31% | With sodium hydride In N,N-dimethyl-formamide at 58 - 62℃; for 3 h; Cooling with ice | (2)Take a concentration of 20percent sodium hydride in DMF, under icecooling,to 2ml / s Was added dropwise with stirring speedof 20percent of the concentration of imidazole in DMF, the reaction was stirred at 60 ° C 60min, after cooling in an ice salt bathmethod, was slowly added to the intermediate product 1, the sodium hydride Of DMF, imidazole in DMF and the weight ratioof the intermediate product as a 7: 7: 5 stirred at 60 ° C in 120min reaction mix, after cooling in an ice salt bath method, areaction solution adding to said reaction mixture 25percent by weight of nhexanewas accounted for the reaction, at a speed of 3rev / sec After stirring for 15min, plus The reaction solution into account the 350percent by weight of the ice, with 3 rev / sec stirreduntil evolution ceased Shen After the precipitate was filtered, the filter cake with accounting for 1/3 times the weight of thefilter cake was washed with water once, in order to speed 2830r / min Conditions centrifugal drying 60min, with the centrifugalaccounted for 2.5 times the weight of the resulting product was dried and 0.05 Times with ethyl acetate and activated carbon,was allowed to stand at 5° C was recrystallized from 13 hours, 50 ° C and By recrystallization of the obtained product wasdried to obtain intermediate 2 detected by HPLC. Intermediate 2 71.5percent yield, wherein the desired product 1(2hydroxy4(4chlorophenyl)butanoic Yl) 1Hydrogen imidazolecontent was 99.31 percent |
99.31% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 30℃; for 1 h; Cooling with ice Stage #2: at 60℃; for 2 h; Cooling with ice |
(1) take 7kg concentration of 20percent sodium hydride DMF solution,Under an ice bath condition, 7kg of imidazole DMF solution with a concentration of 20percent was added dropwise with stirring at a speed of 2ml / s and the reaction was stirred at 60 ° C for 60min; after cooling with an ice-salt bath method, 5kg of 1-chloro-4 - (4-chlorophenyl) -2-butanol stirred at 60 ° C for 120min, cooled with ice salt bath to obtain the reaction solution;(2) Take the reaction solution obtained in the step (1), add n-hexane accounting for 25percent of the weight of the reaction solution, stir for 15 min at a speed of 3 rev / sec, add ice water of 350percent Stirring at a speed of 3 revolutions / second to stop the precipitation precipitation, filtering, washing the filter cake with 1/3 times of the weight of the filter cake for 1 time, centrifuging at the speed of 2825r / min for 60 minutes, The obtained product was 2.5 times in weight and 0.05 times in ethyl acetate and activated carbon, and was allowed to stand at -5 ° C for 13 hours for recrystallization. The product obtained after recrystallization was dried at 50 ° C. After testing, the yield of the product of this example was 71.4percent.Using HPLC and standards on the target product and impuritiesThe amount of testing. After testing,The target product1- (2-hydroxy-4- (4-chlorophenyl) butyl) -1-hydro-imidazoleContent of 99.31percent1- (1-Chloro-4- (4-chlorophenyl) butan-2-yl) -1H-imidazoleContent of 0.57percent4- (4- (1-Hydroxyimidazol-1-yl) phenyl) -1-chloro-2-butanolThe content is 0.08percent. |
99.31% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1 h; Stage #2: at 60℃; for 2 h; |
Take 7kg of 20percent sodium hydride in DMF and add dropwise at 2ml/s in ice bath.7kg concentration of 20percent imidazole in DMF, stirred at 60 ° C reaction 60min;After cooling with an ice salt bath, 5 kg of 1-chloro-4-(4-chlorophenyl)-2-butanol was slowly added, and the reaction was stirred at 60° C. for 120 min. After cooling with an ice salt bath, the reaction liquid was obtained; The reaction solution was added with 25percent by weight of n-hexane, stirred at a rate of 3 revolutions per second for 15 minutes, and then added with ice water of 350percent by weight of the reaction solution and stirred at a rate of 3 revolutions per second to stop. Precipitation precipitation, filtration, filter cake weight 1/3 of the water filter cake washed once, at a speed of 2825r/min centrifugal drying 60min, with the weight of the product obtained by the centrifugal drying 2.5 times and 0.05 times the weight of acetic acid The ethyl ester and the activated carbon were recrystallized at -5°C for 13 hours, and the recrystallized product was dried at 50°C to give 1-(2-hydroxy-4-(4-chlorophenyl)butyl). -1 hydrogen-imidazole, purity 99.31percent. |
88.2% | With sodium hydride In N,N-dimethyl-formamide at 20 - 60℃; for 4.5 h; | (2) Synthesis of 1- (4- (4-chlorophenyl) -2-hydroxybutyl) imidazole. The reaction flask was charged with imidazole and dry DMF. The mass ratio of imidazole to DMF was 24: Adding 3-4 portions of sodium hydride in the next portion, stirring at room temperature till no gas was generated, raising the temperature to 60 ° C, mixing 1-chloro-4- (4-chlorophenyl) -2-butanol with DMF to obtain a mixed solution 3, The mass ratio of 1-chloro-4- (4-chlorophenyl) -2-butanol and DMF in the mixed solution 3 of imidazole and sodium hydride was 24: 7.9: 80: 94.8. The mixed solution was added dropwise to the reaction flask , The dropwise addition was completed for 3.5 hours, the reaction temperature was maintained at 60 ° C, the reaction was continued for 1 hour after the dropwise addition was completed, and then cold water was slowly added until all the solids were precipitated and filtered to obtain 1- (4- (4-chlorobenzene Yl) -2-hydroxy-butyl) imidazole; |
85% | With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water; toluene at 0 - 95℃; for 3 h; | Example 1. Preparation of (1-f4- (4-chlorophenvl)-2-hydroxy-n-butvll-imidazole) (IV); To a solution of 56.7 g (0.26 mol) of 1-chloro-4-chlorophenyl-2-butanol (J. of Medicinal Chemistry, 1978. Vol. 21. No. 8. p. 842) in 200 ml of toluene 36.2 g (0.9 mol) of sodium hydroxide dissolved in 100 ml of water, 6.4 g (0.028 mol) of benzyltriethyammonium chloride and 35.2 g (0.51 mol) of imidazole (III) are added. The reaction mixture is heated at 93-95 °C for one hour then the temperature is returned to about 60 °C, the phases are separated and to the organic layer water (100 ml) is added. The mixture is first stirred at 22-25 °C for 1 hour then at 0-5 °C for two hours. The crystals are separated by filtration, washed with water (2 x 35 ml) of 0-5 °C to yield 74 g of wet (1- [4- (4-chlorophenyl)-2-hydroxy-n-butyl]-imidazole) which is dried at maximum 50 °C in vacuo to give 61.6 g (95 percent) of the product. Recrystallization from ethyl acetate gives 52.4 g (85 percent) of dry product melting at 104-106 °C. |
71.4% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1 h; Cooling with ice Stage #2: at 60℃; for 2 h; Cooling with ice |
(1) Take 7kg of 20percent sodium hydride in DMF. Under ice bath conditions, At a rate of 2 ml/s, 7 kg of a 20percent imidazole DMF solution was added dropwise while stirring. Stir the reaction at 60 ° C 60min; After cooling with ice salt bath, 5 kg of 1-chloro-4-(4-chlorophenyl)-2-butanol is added slowly, Stirring reaction at 60 ° C 120min, after cooling with ice salt bath, the reaction solution; (2) Take the reaction solution obtained in step (1), Add 25percent by weight of the reaction solution of n-hexane, After 15 min stirring at 3 rpm, Then add ice water, which accounts for 350percent of the weight of the reaction solution, Stir at a speed of 3 revs/second to stop precipitation after filtration. Wash the cake once with 1/3 of the weight of the cake, Drying at a speed of 2825r/min for 60min. With ethyl acetate and activated carbon that weighed 2.5 times and 0.05 times the weight of the centrifugally dried product, respectively. After recrystallization at -5°C for 13 hours, the recrystallized product was dried at 50°C to obtain it. Upon detection, the yield of the product of this example was 71.4percent. The target product and impurity levels were determined using HPLC and standards. After testing, The target product, 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1H-imidazole, has a content of 99.31percent. The content of 1-(1-chloro-4-(4-chlorophenyl)butan-2-yl)-1-hydro-imidazole is 0.57percent. The content of 4-(4-(1H-hydrogen-imidazol-1-yl)phenyl)-1-chloro-2-butanol was 0.08percent. |
Tags: 59363-13-2 synthesis path| 59363-13-2 SDS| 59363-13-2 COA| 59363-13-2 purity| 59363-13-2 application| 59363-13-2 NMR| 59363-13-2 COA| 59363-13-2 structure
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