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CAS No. : | 106904-10-3 | MDL No. : | MFCD12025154 |
Formula : | C8H6Cl2O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 253.10 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
73% | With triethylamine In tetrahydrofuran Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride;aluminium trichloride; In dichloromethane; 1,1,2,2-tetrachloroethane; | b) 2,5'-Dichloro-2'-hydroxy-3'-methyl-4-methylsulfonylbenzophenone (Table 1, Example No. 100) 5.06 g of 2-chloro-4-methylsulfonylbenzoyl chloride are added in portions at room temperature to a mixture of 2.85 g of 4-chloro-2-methylphenol and 5.40 g of aluminum chloride in 100 ml of 1,1,2,2-tetrachloroethane, and the mixture is subsequently refluxed for 7 hours. When cold, the reaction mixture is poured onto 200 g of ice and 500 ml of concentrated hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted twice using 50 ml of dichloromethane. The combined organic phases are washed until neutral, dried over magnesium sulfate and evaporated. Recrystallization from a mixture of ethyl acetate and diisopropyl ether gives 4.2 g (60% of theory) of 2,5'-dichloro-2'-hydroxy-3'-methyl-4-methylsulfonylbenzophenone in the form of colorless crystals with a melting point of 175-180 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
COMPOUND 640: 1-[2-chloro-4-(methylsulphonyl)phenyl]-2-cyanopentan-1,3-dione, m.p. 128 C., starting from 3-oxopentanonitrile and 2-chloro-4-(methylsulphonyl)benzoyl chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The compounds listed below may be prepared in manner similar to the method described above. COMPOUND 638: 1-[2-chloro-4-(methylsulphonyl)phenyl]-2-cyano-3-cyclopropylpropan-1,3-dione, m.p. 145 C., starting from <strong>[118431-88-2]3-cyclopropyl-3-oxopropanonitrile</strong> and 2-chloro-4-(methylsulphonyl)benzoyl chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; potassium carbonate; In water; acetonitrile; | EXAMPLE 2 2-(2-Chloro-4-methanesulphonylbenzoyl)-1,3-cyclohexanedione from the acid chloride. 2-Chloro-4-methanesulphonylbenzoyl chloride (5 g) was prepared by the reaction of 2-chloro-4-methanesulphonylbenzoic acid with thionyl chloride. The acid chloride was dissolved in acetonitrile (40 ml). A mixture of 1,3-cyclohexanedione (2.24 g), potassium carbonate (6.9 g) and acetonitrile (40 ml) was stirred at room temperature for 4 hours. To this solution was added the acid chloride solution over 10 min and allowed to stir 1 hour. 1,2,4-Triazole (0.07 g) was then added and the mixture allowed to stir 16 hours at room temperature. The solvent was removed and the residue was dissolved in water and acidified. The product was extracted into dichloromethane and the solvent was dried then evaporated to give the desired product in 83.6percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With thionyl chloride; N,N-dimethyl-formamide; In toluene; at 0 - 50℃; for 27h; | Four-necked flask add the compound 4- (methylsulfonyl) -2-chloro-benzoic acid 100g (0.426mol), toluene was added 500mL (not all dissolved at room temperature), add with stirring a catalytic amount of dimethylformamide 2mL. Installing a gas absorption device, was cooled to 0 deg.] C, slowly dropwise thionyl chloride 100g (0.84mol), was added dropwise need 3h, during the addition to maintain the temperature below 5 . After the dropwise addition, heated slowly to 50 (mixture was gradually clarified, and finally clear solution is formed), the reaction 24h, TLC detection reaction process (developing solvent: ethyl acetate). Rotary evaporation to remove the solvent and excess thionyl chloride to give a residue 105g, a yield of 97%, without further purification, was used directly in the next reaction. |
With thionyl chloride; at 70℃; for 1h; | <strong>[53250-83-2]2-chloro-4-(methylsulfonyl)benzoic acid</strong> (300 mg, 1.28 mmol) was dissolved in 5 ml of thionyl chloride and the reaction mixture was heated to 70 0C for 1 hour. The reaction mixture was concentrated down under reduced pressure, and the <n="265"/>white solid was dissolved in 5 ml of pyridine, and 3-amino-5-bromobenzofuran-2- carboxamide 3 ( 315 mg, 1.24 mmol) was added at room temperature. The reaction was stirred at room temperature for 1 hr, followed by addition of 10 ml of MeOH. The resulting precipitate was filtered off and dissolved in 3 ml of EtOH. The reaction was stirred for 12 hours at 120 0C in a sealed pressure tube. The reaction was cooled and then neutralized with IM HCl until the pH 7. The resulting precipitate was filtered and washed with 5 ml OfH2O. The product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% NH40Ac/Ac0H) to yield 34.7 mg (12%) of the title compound. 1H NMR (400 MHz, d6-DMSO): 13.49 (s, IH), 8.25 (d, IH), 8.21 (d, IH), 8.07 (dd, IH), 8.00 (d, IH), 7.89 (m, 2H), 3.41 (s, 3H); MS (EI) for Ci7Hi0BrClN2O4S: 455 (MH+). | |
With thionyl chloride; for 3h;Reflux; | Example 5 Preparation: <strong>[53250-83-2]2-chloro-4-(methylsulfonyl)benzoic acid</strong> ( 62mg, 0.26 mmol) was added into 3 ml_ SOCI2, and then reflux for 3 h, removed the solvents to obtain white solid. Dried on vacuum for 30 min, and then used at next step without purification |
In a reactor fitted with an agitator, condenser, and scrubber with 10% sodium hydroxide solution, toluene (500ml) was charged followed by the 2-chloro-4- sulfomethylbenzoic acid (10Og) and catalytic amount of DMF (2ml). The reaction mixture was cooled to 0 0C and thionyl chloride (5Og) was added slowly over a period of 3 hours keeping the temperature below 5 0C. The reaction mixture was slowly heated to 50 0C allowing the HCl and SCh formed to escape into the scrubber.The end of the reaction was determined by absence of acid. The solvent was distilled off along with the excess thionyl chloride used for the reactor. The residue thus obtained (105 g) was used directly for the next step. | ||
With thionyl chloride; In dichloromethane; at 0 - 20℃; for 0.5h; | In 50ml eggplant-shaped flask, 1.50mmol <strong>[53250-83-2]2-chloro-4-methanesulfonylbenzoic acid</strong> was dissolved in 15ml of dichloromethane, the ice bath was Cooled to 0 ~ 5 C, was added dropwise 3.0mmol thionyl chloride, at room temperature after stirring for 30min, and excess dichloromethane was removed by rotary evaporation the thionyl chloride, 15ml of anhydrous tetrahydrofuran was added, the ice bath was cooled to 0 ~ 10 C, a solution of 4-chloro-3-(pyridin-2-yl)aniline (1.47mmol / 10ml) in THF, dropwise added triethylamine 2.5mmol then finished, and after dropping in often Temperature reaction 4h, the reaction was complete, the reaction was poured into 50ml of water and stirring, the precipitated solid was filtered, washed with water, dried Dryness, to give a white solid product, yield 88%. | |
With thionyl chloride; In dichloromethane; at 0 - 20℃; for 0.5h; | In a 50 ml Erlenmeyer flask, 1.50 mmol of <strong>[53250-83-2]2-chloro-4-methanesulfonylbenzoic acid</strong> was dissolved in 15 ml of dichloromethane and the ice bath was cooled to 0 to 5 C,A solution of 3.0 mmol of thionyl chloride was added dropwise at room temperature for 30 min, followed by rotary evaporation to remove methylene chloride and excessOf thionyl chloride,A solution of 4-chloro-3- (rho-pyridin-2-yl) aniline in anhydrous THF (1.47 mm / l 10 ml) was added dropwise to a solution of 15 ml of anhydrous tetrahydrofen ),After the addition of 2.5 mml of triethylamine, the reaction was carried out at room temperature for 4 hours. The reaction was completed and the reaction system was poured into 50 ml of water and stirred to precipitate a solid, filtered, washed with water and dried to give The white solid product yielded 88%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With triethylamine In dichloromethane at 0 - 20℃; for 8h; | 4 2- (2-chloro-5-aminophenyl) pyridine (IV, 0.061 g, 0.3 mmol) was dissolved in dichloromethane,2-Chloro-4-methylsulfone benzoyl chloride (0.091 g, 0.36 mmol) was added at 0 ° C,Followed by the addition of triethylamine (0.036 g, 0.36 mmol) and slowly to room temperature for 8 hours.After the reaction, the solvent was removed, extracted with ethyl acetate, washed with water, dried and purified by column chromatography.get2-Chloro-N- (4-chloro-3- (2-pyridyl) phenyl) -4-methylsulfone phenylbenzamide (V, Erivedge)0.130 g, yield 92%.Experiments show that the solvent used in this example (the third solvent) can also be replaced with tetrahydrofuran or dichloroethane.The base may be treated with pyridine, sodium carbonate or potassium carbonate at room temperature for 5 hours,The extraction agent may also be used in dichloromethane. |
92% | With sodium carbonate In dichloromethane at 20℃; for 0.333333h; Cooling with ice; | 4 Example 4Preparation of Vimodedji Dichloromethane (150 ml) was added to the reaction flask.Compound B (18.47 g, 0.09 mol),Anhydrous sodium carbonate (14.3 g, 0.14 mol),At room temperature,2-Chloro-4-(methylsulfonyl)benzoyl chloride (22.78 g, 0.09 mol)Soluble in dichloromethane (50ml),Add dropwise to the above reaction bottle, drop,React to room temperature at room temperature,Add ice water,After stirring for 20 minutes,Dispensing, washing the organic phase 3 times,The organic phase is concentrated to dryness under reduced pressure.Recrystallization using 90% ethanol (80 ml),The dried Vimodex (34.88 g, 92%) was filtered. |
92.2% | With potassium carbonate In dichloromethane at 15 - 20℃; for 1h; | 6 Example 6: Preparation of vismodegib (I) Into a 500 mL four-necked flask was added 150 g of dichloromethane, 20.5 g (0.1 mol) of 2-(2-chloro-5-aminophenyl)pyridine prepared according to the method of Example 3, and 12.0 g of anhydrous potassium carbonate, maintaining the temperature At 15-20°C, a solution containing 25.3 g (0.1 mol) of 2-chloro-4-methylsulfonylbenzoyl chloride and 100 g of dichloromethane was added dropwise. After the completion of the drop, the reaction was incubated for 1 hour.After the amidation reaction is completed, add 50 grams of ice water, stir for 30 minutes, separate the layers, and wash the organic phase 3 times with 20 grams each time. Take the organic phase and collect the solvent under reduced pressure to dryness. 38.8 grams of vismodegib, the liquid phase purity is 99.9%, and the yield is 92.2%. |
91.5% | With sodium carbonate In dichloromethane at 15 - 20℃; for 1h; | 8 Example 8: Preparation of vismodegib (I) To a 500 mL four-necked flask, 150 g of methylene chloride and 20.50 g of 2- (2-chloro-5-aminophenyl) pyridine were added,Anhydrous sodium carbonate 11g, maintaining the temperature at 15-20 , dropping 2-chloro-4-methylsulphonylbenzoyl chloride 25.32g of dichloromethane solution 100g, dropping completed, incubated for 1h.After the acylation reaction is completed, dd ice water 50g, stirred for 30min, stratified, the organic phase was washed 3 times, the organic phase was taken, the solvent was evaporated to dryness under reduced pressure, 60g of 90% ethanol was added for recrystallization to obtain 38.79g of vismodegib with HPLC purity of 99.96% Yield 91.5%. |
88% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 4h; | 8 Preparation of Vismodegib In 50ml eggplant-shaped flask, 1.50mmol 2-chloro-4-methanesulfonylbenzoyl chloride in 15ml of anhydrous tetrahydrofuran, The ice bath was cooled to 0 ~ 10 ° C, dry tetrahydrofuran was added dropwise a solution of 4-chloro-3-(pyridin-2-yl)aniline (1.47mmol / 10ml), After dropping then added triethylamine 2.5mmol of dropwise addition, the reaction at room temperature 4h, the reaction was completed, the reaction system down Into 50ml water and stirred, the precipitated solid was filtered, washed with water, and dried to give a white solid, yield 88%. |
88% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 4h; | 12 Preparation of Vismodegib In a 50 ml Erlenmeyer flask, 1.50 mmol of 2-chloro-4-methanesulfonylbenzoyl chloride was dissolved in 15 ml of anhydrous tetrahydrofuran, and the ice bath was cooled to 0 to 10 ° C,A solution of 4-chloro-3- (pyridin-2-yl) aniline in anhydrous tetrahydrofuran (1.47 mmol / 10 ml)After the addition of 2.5 mmol of triethylamine, dropwise,After reaction at room temperature for 4 h, the reaction was completed. The reaction was poured into 50 ml of water and stirred. The solid was precipitated, filtered, washed with water and dried to give a white solid product in 88% yield. |
68% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 4h; | |
52% | With triethylamine In tetrahydrofuran at 0 - 4℃; for 17h; | I; II; III Synthesis of Vismodegib (5) 96.3 mg of intermediate 3 (0.47 1 mmol) has been dissolved inS mE THF and the resulting solution was cooled in an ice-bath. To the cooled solution of intermediate 3, a beforehand prepared solution of intermediate 4 (122.4 mg, 0.47 1 mmol) in 5 mE THF was added. Then, 0.35 mE NEt3 was added to the resulting suspension and the mixture was allowed to stir for 17 h at 0-4° C. After completeness of the reaction, the solvent was evaporated under reduced pressure (rotavap 50° C.) and the residual solid was suspended in 5 mE saturated NaHCO3 solution. Extraction with 3x5 mE of DCM and subsequent evaporation of the organic solvent yielded 194.3 mg of crude Vismodegib (off-white). The crude material was then purified via colunm chromatography over silica gel, which yielded in 103.5 mg pure Vismodegib (off-white to yellow solid, 52%). 1H-NMR (500 MHz, CD2C12): 9.51 (s, ‘H), 8.44(ddd, J=4.9, 1.8 and 1.0Hz, 1H), 8.01 (dd, J=8.8 and 2.7 Hz,1H), 7.89 (d, J=1.7 Hz, 1H), 7.74 (dd, J=1.8 and 1.1 Hz, 1H),7.73-7.71 (m, 2H), 7.86 (dt, J=7.9 and 1.1 Hz, 1H), 7.59 (d,J=8.0, 1H), 7.51 (d, J=8.7 Hz, 1H), 7.22 (ddd, J=7.5, 4.9 and1.3 Hz, 1H), 2.98 (s, 3H). |
109 mg | With triethylamine In tetrahydrofuran at 0 - 20℃; for 16h; | |
With potassium carbonate In tetrahydrofuran; water at 2 - 20℃; Large scale; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Embodiments substantially the same manner as in Example 1, difference is that the in Table 1. 220mL1,2- dichloroethane was added anhydrous aluminum chloride powder 30.8g (0.23mol) was stirred for 30 minutes (1,2-dichloroethane and after mixing anhydrous aluminum chloride, the solution turned yellow) , then 4- (methylsulfonyl) -2-chlorobenzoyl chloride 19.23g (0.076mol) (yellow precipitate appears) and stirring continued for 30 minutes. After then added bicyclo [3.2.1] 2,4-dione 10.5g (0.076mol), heated reactor, the internal temperature was raised to 58 (added bicyclo [3.2.1] -2,4-dione, The precipitate gradually dissolved into a clear solution, the color of soy sauce). Stirring was continued for 3 hours, TLC detection reaction process (developing solvent: ethyl acetate). After completion of the reaction, cooled to room temperature, and after cooled with ice continues, 6N hydrochloric acid was added dropwise with stirring 178mL. The organic layer was separated and the aqueous layer was extracted with 110mL of 1,2-dichloroethane. The combined organic layer was concentrated under reduced pressure to remove the solvent, and then methanol was added 120mL dissolved by heating (inner temperature 62 deg.] C), and then 22mL of 6N hydrochloric acid was added dropwise over 15 minutes. Stirred for 1 hour at 62 , stirred at room temperature overnight. The desired product precipitated by suction filtration, the solid washed with methanol / water = 25: 1 to give the product 24g is recrystallized product yield of 89%. As determined by HPLC area percentage (purity) of 98.42%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(1) in a nitrobenzene solution having a concentration of 40% by weight of 2-chloro-4-methanesulfonylbenzoyl chloride,Adding catalyst ferric chloride, heating to 40 C, and then performing a complexation reaction for 1 h;The molar ratio of the ferric chloride to the 2-chloro-4-methylsulfonylbenzoyl chloride is 1:1;(2) Cool down to 22 C,To the reaction system of the step (1), a nitrobenzene solution of <strong>[74896-14-3]bicyclo[3.2.1]octane-2,4-dione</strong> at a concentration of 40% by weight is directly added.After pre-reaction for 1 h,The temperature was raised to 52 C for acid chloride substitution reaction for 2.0 h.After cooling the product of the acid chloride substitution reaction to 8 C,Adding 3 mol/L aqueous hydrochloric acid solution, stirring, and filtering, the filter residue is a crude product of dicyclohexyl ketone;The molar ratio of the bisbenzene [3.2.1] octane-2,4-dione nitrobenzene to 2-chloro-4-methylsulfonylbenzoyl chloride is 1:1.2; |
Tags: 106904-10-3 synthesis path| 106904-10-3 SDS| 106904-10-3 COA| 106904-10-3 purity| 106904-10-3 application| 106904-10-3 NMR| 106904-10-3 COA| 106904-10-3 structure
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H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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