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[ CAS No. 53250-83-2 ]

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Chemical Structure| 53250-83-2
Chemical Structure| 53250-83-2
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CAS No. :53250-83-2 MDL No. :MFCD00216496
Formula : C8H7ClO4S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :234.66 g/mol Pubchem ID :735863
Synonyms :

Safety of [ 53250-83-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53250-83-2 ]

  • Upstream synthesis route of [ 53250-83-2 ]
  • Downstream synthetic route of [ 53250-83-2 ]

[ 53250-83-2 ] Synthesis Path-Upstream   1~11

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YieldReaction ConditionsOperation in experiment
46.6% With hydrogenchloride; sodium chlorite In water; acetonitrile at 0 - 80℃; for 1 h; Acetonitrile (4 ml) and compound 5 (100 mg, 0.46 mmol) were added to a 10 ml three-necked flask and stirred until dissolved.After cooling to 0°C, add NaClO2 (124 mg,1.38 mmol) of an aqueous solution of 1 ml and HCl (117 μL) was stirred for 0.5 h and then warmed to 80° C. and stirring was continued for 0.5 h.After the reaction was monitored by TLC, the mixture was cooled to room temperature, and the mixture was dried on acetonitrile, adjusted to pH 2 with 1N HCl aqueous solution, and extracted with ethyl acetate/water.The organic phase was obtained, and the organic phase was dried over anhydrous Na 2 SO 4 , and the organic solvent was removed by rotary drying to obtain a crude product. The crude product was purified by column chromatography and petroleum ether:ethyl acetate (glacial acetic acid)=1:1 (5 Torr) was eluted to give Compound 32. White solid 50 mg, 46.6percent yield.
Reference: [1] Patent: CN107556289, 2018, A, . Location in patent: Paragraph 0142; 0144; 0145; 0146
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YieldReaction ConditionsOperation in experiment
94.3% at 160℃; 117 g of 2-chloro-4-methylsulfonyltoluene obtained in step 1) and 75 g of 40percent phosphoric acid were added to a 500 ml four-necked flask;After stirring to raise the temperature to 160 ° C, dilute nitric acid with a concentration of 68percent (ie 15.2 mol / L) was slowly added dropwise;During the dropwise addition, the temperature was kept at 160 ° C;Reaction to the end, stop adding dilute nitric acid;After the reaction was completed, the water was slowly added to the reaction mixture, stirred and cooled for about 30 minutes at room temperature, filtered,The filter cake was washed, the washed material was added to a 1000ml four-necked flask equipped with 400g of water,Then add dichloroethane refined filter (dichloroethane added amount of 2-chloro-4-methylsulphenyl toluene quality of 1.8 times)124g of white crystals of 2-chloro-4-methylsulphonylbenzoic acid dried in an amount of 99.0percent or more,The final molar yield of 2-chloro-4-methylsulfonylbenzoic acid was found to be 94.3percent.
87.5% at 180℃; for 4.2 h; Autoclave Table 1
1), 5.15 g (0.025 mol) of 2-chloro-4-methylsulfonyltoluene,12.60 g (0.050 mol) of 25 wtpercent nitric acid,Catalyst CuI (0.00125 mol) 0.24 g,Co2O3 (0.00125mol) 0.21g sequentially added 25mL autoclave,Feed is completed, the autoclave filled with oxygen pressure of 3.0MPa,Slowly warmed to 200 ° C (about 12 minutes to complete warming),Insulation stirring reaction 1h,At this point the system pressure dropped to 1.8MPa,Then re-filled with oxygen pressure of 3.0MPa,Continue to heat the reaction for about 3h.
2), stop heating,Continue to stir,The reaction product obtained in step 1) was naturally cooled to room temperature,Pressure relief (a small amount of yellow smoke)The reaction product was transferred to a 100 mL beaker,Slowly added dropwise 20wtpercent NaOH solution 20g (about 10 minutes dropwise added)The reaction product was stirred until no solid was dissolved.Filter, get cake (trace, for disposal),The filtrate was adjusted to pH = 2 using 36 wtpercent hydrochloric acid,Precipitation of a large number of light yellow solid, dried at 80 5h,A solid (crude 2-chloro-4-methylsulfonylbenzoate) was obtained in an amount of 5.05 g,Yield 86.3percent (based on 2-chloro-4-methylsulphenyl toluene,The same below), HPLC detection of product content 95.8percent.
3), crude 2-chloro-4-methylsulphonyl benzoic acid (referred to as crude) was recrystallized from anhydrous methanol thermal dissolution method,Crude and methanol mass ratio of 1: 2,That 1g crude with 2mL anhydrous methanol,To the crude product was added anhydrous methanol,Heat (about 64-65 ° C) until the crude product is completely dissolved,Allow to cool to room temperature.A light yellow solid precipitated,Decompression (0.1MPa pressure) suction filtration,The filter cake was dried at 80 ° C for 5h,Weighing, in solid --- 2-chloro-4-methylsulfonyl benzoic acid 4.54g,Yield 77.6percent, HPLC detection of product content 99.2percent.
84.2% at 160℃; for 4.7 h; Autoclave 2-Chloro-4-(methylsulfonyl)toluene (0.100 mol, 20.50 g), CuI (0.001 mol, 0.19 g) and 25 wtpercent HNO3 (12.60 g) were added in sequence to a 100 mL high pressure reaction kettle equipped with stirrer and a temperature measuring device. Oxygen gas filled the kettle until the pressure was 1.5 MPa. The reaction solution was heated to 160 C slowly (approximately 0.7 h). The autoclave pressure was raised to 2.5 MPa. The reaction was continued for 4 h with stirring at keeping 160 C (thermostated). At the conclusion of the reaction the pressure declined to 0.8 MPa and was stable (9 molpercentNO2 and 5 molpercent NO, gaseous species concentration determined by the concentration of NO2- and NO3- after passing the gas through NaOH solution). Thin layer chromatography (TLC) was used to determine reaction conversions in some instances. After the reaction was finished, a 25 wtpercent NaOH solution (0.200 mol NaOH) was added into the reaction solution and stirring was continued. After reduced pressure filtering, 36 wtpercent hydrochloric acid was used to adjust the pH of the filtrate to pH 2. The resulting precipitate was collected by filtration. This precipitate was added to MeOH (110 mL) containing 3.00 g of activated carbon. The mixture was heated gently to reflux temperature (60 C). The precipitate dissolved completely. Stirring was continued for 1 h. The mixture was filtered, and allowed to cool at 10 C. After 8 h at -5 C the reaction was filtered. The solid precipitate was dried at 80 C for 5 h to give 19.70 g (0.084 mol) of the product as white crystals. The yield was 84.2percent and the product purity was 99.7percent.
Reference: [1] Patent: CN104086466, 2017, B, . Location in patent: Paragraph 0022-0024; 0032; 0040
[2] Patent: CN105017101, 2017, B, . Location in patent: Paragraph 0005; 0039; 0040; 0042-0046
[3] Chemical Papers, 2018, vol. 72, # 1, p. 51 - 56
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Reference: [1] Patent: US5008448, 1991, A,
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Reference: [1] Patent: US5783729, 1998, A,
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Reference: [1] Patent: US5175351, 1992, A,
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Reference: [1] Patent: US5175351, 1992, A,
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Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 16, p. 8716 - 8724
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Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 16, p. 8716 - 8724
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Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 16, p. 4974 - 4976
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Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 16, p. 4974 - 4976
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Reference: [1] Patent: US5318947, 1994, A,
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