Structure of 94291-61-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 94291-61-9 |
Formula : | C20H20N2O2 |
M.W : | 320.39 |
SMILES Code : | N#CC1=CC=C(OCCCCCCOC2=CC=C(C=C2)C#N)C=C1 |
MDL No. : | MFCD01529716 |
InChI Key : | NSIXQDMKFBNVGX-UHFFFAOYSA-N |
Pubchem ID : | 4417701 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
With trifluoroacetic acid; In toluene; at 10 - 38℃; for 43h;Industrial scale; | To the reaction flask by adding intermediate product I 70g (0.22mol), ethanol 400 ml, toluene 1260 ml, stirring in 10 C the following by adding trifluoroacetic acid 87g (of the total amount of the reaction system 5.3%), elevation of temperature in 38 C reaction 43h time, TLC detection intermediate I raw material has completely disappeared, the reaction end, cold to 10 C the following, filtering, drying, the white solid obtained 85.31 g. Yield 94% | |
With hydrogenchloride; In chloroform; water; at 10 - 30℃; for 72h; | In a 250 ml three-necked flask, a mechanical stirrer, a thermometer and a gas pipe were installed, and 14.0 g of <strong>[94291-61-9]4,4'-dicyano-1,6-diphenoxyhexane</strong> and 100 ml of absolute ethanol were successively added, stirred and cooled 10 or less;Anhydrous HCl gas was introduced into the reaction system after drying with anhydrous CaCl2 to control the aeration speed and keep the reaction temperature between 10 and 15 C until the weight of the reaction system was increased to 20.4g.Ventilation is completed, add 100ml of chloroform, the temperature was maintained at between 25 ~ 30 , continuous reaction 72 hours;The reaction was cooled to below 10 C, stirred overnight and filtered. The filter cake was washed with cold chloroform and dried to give 29.45 g of a white product in a yield of 89.35%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.52% | Weigh 20.36gNa was added to a 250ml three-necked flask containing 25ml of ethanol until Na was completely dissolved.To this, 200 ml of an ethanol solution containing 51.0 g of p-cyanophenol was added dropwise to control the feeding rate so that the reaction temperature was maintained at 25 to 30,After the addition was completed, the mixture was slowly heated to reflux. After 1 hour of reaction, 40.4 g of 1,6-dibromohexane was added dropwise to the reaction system to control the feeding rate. After completion of the addition, the reaction was carried out for 3 hours.After the reaction was completed, the temperature was lowered to below 10 , stirred for 2 hours, filtered and the filter cake was dried to give 55.4g of white powder. Yield: 94.52%. | |
81% | In with stirring, thermometer, a reflux condenser of the dropping funnel and 2L in three-mouth bottle, to which in turn is added to sodium hydroxide 23.3g (0.56mol) and water 240 ml, after stirring to make it dissolve completely, cooling to room temperature; the instillment contains 66.7g (0.56mol) 4-cyano phenol 267 ml ethanol solution, control drop of acceleration, keeping the temperature at the 25-30 C; after dripping slowly increase, 80 C reaction 2h, cooling to room temperature; dropwise 65.3g (0.27mol) 1,6- two hexyl bromides, reflux (80-85 C) 8-10h, cooling to 0 C, stirring 2-3h, filtered, white solid product I shall be intermediate 98g, to the wet product 417 ml in ethanol, heating and stirring to 75 C reflux reaction 2-3h, cooling, about 50 C the left and right filter, drying filter cake, weighing more 70.01g, yield 81%. |