Alternatived Products of [ 57753-80-7 ]
Product Details of [ 57753-80-7 ]
CAS No. : | 57753-80-7 |
MDL No. : | |
Formula : |
C11H6Cl2O2
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
241.07
|
Pubchem ID : | - |
Synonyms : |
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Safety of [ 57753-80-7 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 57753-80-7 ]
* 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.
- Upstream synthesis route of [ 57753-80-7 ]
- Downstream synthetic route of [ 57753-80-7 ]
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Yield | Reaction Conditions | Operation in experiment |
|
With thionyl chloride; In benzene; for 3h;Reflux; |
General procedure: A mixture of 5-substituted phenyl-2-furancarboxylic acid (0.05 mol) and thionyl chloride (0.15 mol) was refluxed in anhydrous benzene for 3 h. The excess of thionyl chloride and the solvent were distilled off. The residues were dissolved in anhydrous benzene. The solution of 5-substituted phenyl-2-furancarbonyl chloride in anhydrous benzene was added into thymol or carvacrol. The mixture was stirred and refluxed for 5 h. After cooling, the solvent was evaporated off under reduced pressure, and the solid was recrystallized from ethanol to obtain the title compounds I and II. |
|
With thionyl chloride; In toluene; for 3.5h;Reflux; |
Chemical synthesis The synthetic route of title compounds 3a-3o (containing 1,2,3,4-tetrahydroquinoline), 4a-4o (containing 1,2,3,4-tetrahydroisoquinoline) and 5a-5o (containing 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline) was described in Scheme 1 . The key intermediates 2 (the different carboxylic acids 2) were synthesized from substituted aniline by Meerwein arylation reaction according to the reported procedure [31,33]. Then a mixture of 5-substitutedphenyl-2-furancarboxylic acid 2 and thionyl chloride was refluxed in anhydrous toluene for 3.5?h to afford the various 5-phenyl-2-furancarbonyl chloride, which was added into tetrahydroquinoline in anhydrous dichloromethane to react and obtain the title compounds 3 (3a-3o). |
|
With thionyl chloride; |
The 5-(p-chlorophenyl)-2-furoyl chloride used in this example was obtained by reaction of 5-(p-chlorophenyl)-2-furoic acid and thionyl chloride. |
|
With thionyl chloride; In 1,2-dichloro-ethane; at 120℃; |
General procedure: To a solution of 5-(3,4-difluorophenyl)furan-2-carboxylic acid (40 mg, 0.18 mmol) was added thionyl chloride (0.02 ml, 0.9 mmol) in 1,2-dichloroethane (1 mL), the reaction mixture were stirred for 30 min. After evaporating solvent, tert-butyl 4-(2-chloro-4-(piperazin-1-ylmethyl)phenoxy)piperidine-1-carboxylate 7 (82 mg, 0.20 mmol) and triethylamine (0.075 ml, 0.54 mmol) added crude acid chloride in dichloromethane. After being stirred at room temperature for 2 h, the mixture was diluted with water (30 mL), and extracted with dichloromethane (30 mL x 2). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo, giving a residue that was subjected to column chromatography on silica gel (3% MeOH/CH2Cl2) to afford 98 mg (89%) of the boc-protected compound. |
Reference:
[1]Russian Journal of Organic Chemistry,2009,vol. 45,p. 541 - 550
[2]Collection of Czechoslovak Chemical Communications,1984,vol. 49,p. 1505 - 1514
[3]Journal of Medicinal Chemistry,2007,vol. 50,p. 1850 - 1864
[4]Journal of Medicinal Chemistry,2008,vol. 51,p. 407 - 416
[5]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6379 - 6386
[6]Molecules,2010,vol. 15,p. 4267 - 4282
[7]Chinese Journal of Chemistry,2010,vol. 28,p. 1233 - 1239
[8]Chinese Journal of Chemistry,2010,vol. 28,p. 1257 - 1266
[9]Chemical Biology and Drug Design,2012,vol. 79,p. 121 - 127
[10]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 11649 - 11656
[11]Letters in drug design and discovery,2014,vol. 11,p. 877 - 885
[12]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3632 - 3635
[13]European Journal of Medicinal Chemistry,2018,vol. 151,p. 546 - 556
[14]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3271 - 3275
[15]Patent: US4128550,1978,A
[16]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 577 - 580
[17]Journal of Agricultural and Food Chemistry,2019
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[ 75129-74-7 ]
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[ 2381-75-1 ]
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[ 1147550-11-5 ]
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5-(4-chloro-phenyl)-furan-2-carbonyl isothiocyanate
[ No CAS ]
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[ 57753-80-7 ]
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[ 120908-70-5 ]
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(1-benzo[1,3]dioxol-5-yl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-[5-(4-chloro-phenyl)-furan-2-yl]-methanone
[ No CAS ]
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[ 57753-80-7 ]
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[ 21103-33-3 ]
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5-(4-chlorophenyl)-N-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl)furan-2-carboxamide
[ No CAS ]
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[ 74115-12-1 ]
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[ 57753-80-7 ]
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C16H9Cl2NO3
[ No CAS ]
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[ 57753-80-7 ]
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[ 364331-60-2 ]
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[ 57753-80-7 ]
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1-phenyloxyacetyl-4-(5-(4-chlorophenyl)-2-furoyl)semicarbazide
[ No CAS ]
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[ 57753-80-7 ]
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1-(4-methylphenyloxyacetyl)-4-(5-(4-chlorophenyl)-2-furoyl)semicarbazide
[ No CAS ]
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[ 57753-80-7 ]
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1-(2-methylphenyloxyacetyl)-4-(5-(4-chlorophenyl)-2-furoyl)semicarbazide
[ No CAS ]
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[ 57753-80-7 ]
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1-(4-chlorophenyloxyacetyl)-4-(5-(4-chlorophenyl)-2-furoyl)semicarbazide
[ No CAS ]
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1-(4-methoxyphenyloxyacetyl)-4-(5-(4-chlorophenyl)-2-furoyl)semicarbazide
[ No CAS ]
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[ 364331-66-8 ]
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1-(4-nitrophenyloxyacetyl)-4-(5-(4-chlorophenyl)-2-furoyl)semicarbazide
[ No CAS ]
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1-(2-nitrophenyloxyacetyl)-4-(5-(4-chlorophenyl)-2-furoyl)semicarbazide
[ No CAS ]
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1-(3-nitrophenyloxyacetyl)-4-(5-(4-chlorophenyl)-2-furoyl)semicarbazide
[ No CAS ]
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1-(1-naphthyloxyacetyl)-4-(5-(4-chlorophenyl)-2-furoyl)semicarbazide
[ No CAS ]
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[ 364331-74-8 ]
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N-(5-phenyloxymethyl-1,3,4-thiadiazol-2-yl)-N'-(5-(4-chlorophenyl)-2-furoyl)-thiourea
[ No CAS ]
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[ 57753-80-7 ]
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N-(5-(2-methylphenyloxymethyl)-1,3,4-thiadiazol-2-yl)-N'-(5-(4-chlorophenyl)-2-furoyl)-thiourea
[ No CAS ]
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[ 57753-80-7 ]
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N-(5-(3-methylphenyloxymethyl)-1,3,4-thiadiazol-2-yl)-N'-(5-(4-chlorophenyl)-2-furoyl)-thiourea
[ No CAS ]
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[ 57753-80-7 ]
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N-(5-(4-methoxyphenyloxymethyl)-1,3,4-thiadiazol-2-yl)-N'-(5-(4-chlorophenyl)-2-furoyl)-thiourea
[ No CAS ]
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[ 57753-80-7 ]
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N-(5-(4-methylphenyloxymethyl)-1,3,4-thiadiazol-2-yl)-N'-(5-(4-chlorophenyl)-2-furoyl)-thiourea
[ No CAS ]
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[ 57753-80-7 ]
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N-(5-(2,4-dichlorophenyloxymethyl)-1,3,4-thiadiazol-2-yl)-N'-(5-(4-chlorophenyl)-2-furoyl)-thiourea
[ No CAS ]
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[ 92972-94-6 ]
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[ 93770-52-6 ]
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[ 57-14-7 ]
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5-(p-Chlorophenyl)-2-furoic Acid 2,2-Dimethylhydrazide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
48 g (73%) |
In benzene; |
EXAMPLE II 5-(p-Chlorophenyl)-2-furoic Acid 2,2-Dimethylhydrazide To a solution of 36 g (0.60 mole) of dimethylhydrazine and 150 ml of benzene was added portionwise 60 g (0.25 mole) of <strong>[57753-80-7]5-(p-chlorophenyl)-2-furoyl chloride</strong> with the temperature being controlled below 50 by means of an ice bath. The reaction mixture was refluxed for 2 hours with dissolution, cooled and the resulting precipitate filtered, washed with water and dried at 60 to yield 48 g (73%). An analytical sample was prepared by recrystallizing a sample from ethyl acetate/Darco and drying in the vacuum pistol at room temperature, m.p. 150-152. Anal. Calcd. for C13 H13 ClN2 O2: C, 58.98; H, 4.95; N, 10.58. Found: C, 58.70; H, 5.05; N, 10.33. |
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ethereal HCl
[ No CAS ]
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[ 57753-80-7 ]
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concentrated NH4 OH
[ No CAS ]
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[ 69333-29-5 ]
Yield | Reaction Conditions | Operation in experiment |
|
In water; toluene; |
EXAMPLE I 1-Methyl-4-piperidyl 5-(p-chlorophenyl)-2-furoate Hydrochloride To a stirring solution of 40 g (0.35 mole) of N-methyl-4-piperidol in 400 ml of toluene was added portionwise 84 g (0.35 mole) of <strong>[57753-80-7]5-(p-chlorophenyl)-2-furoyl chloride</strong> with the temperature rising to 50. The resulting mixture was heated at 90 for 1 hour and then stirred at room temperature overnight. The solid was filtered, suspended in H2 O and acidity assured by the addition of a few drops of hydrochloric acid. The insoluble material was filtered. The filtrate was made basic by the addition of concentrated NH4 OH. The resulting solid was filtered and added to 1500 ml of ether with dissolution. The solution was treated with Darco, dried with MgSO4 and filtered. The filtrate was treated with ethereal HCl. A "sticky" solid formed from which the ether was decanted. The semi-solid was triturated in ethanol with a white solid forming which weighed 50 g (40%) after drying. |
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[ 1007197-82-1 ]
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[ 129488-00-2 ]
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[ 57753-80-7 ]
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C24H23ClN2O4
[ No CAS ]
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[ 580-15-4 ]
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5-(4-chlorophenyl)-N-(quinolin-6-yl)furan-2-carboxamide
[ No CAS ]
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[ 50533-97-6 ]
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[ 41838-46-4 ]
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[ 53369-71-4 ]
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[ 57260-71-6 ]
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[ 927570-11-4 ]
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[ 57753-80-7 ]
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[ 333-20-0 ]
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5-(4-chloro-phenyl)-furan-2-carbonyl isothiocyanate
[ No CAS ]
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[ 60336-09-6 ]
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[ 7400-27-3 ]
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Reference:
[1]Chemical Biology and Drug Design,2012,vol. 79,p. 121 - 127
[2]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 11649 - 11656
[3]Letters in drug design and discovery,2014,vol. 11,p. 877 - 885
[4]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3632 - 3635
[5]European Journal of Medicinal Chemistry,2018,vol. 151,p. 546 - 556
[6]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3276 - 3280
[7]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3271 - 3275
[8]Journal of Agricultural and Food Chemistry,2019
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[ 106-47-8 ]
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[ 57753-80-7 ]
Reference:
[1]Chemical Biology and Drug Design,2012,vol. 79,p. 121 - 127
[2]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 11649 - 11656
[3]Letters in drug design and discovery,2014,vol. 11,p. 877 - 885
[4]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3632 - 3635
[5]European Journal of Medicinal Chemistry,2018,vol. 151,p. 546 - 556
[6]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3276 - 3280
[7]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3271 - 3275
[8]Journal of Agricultural and Food Chemistry,2019
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[ 100-52-7 ]
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[ 1145781-20-9 ]
- 78
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[ 57753-80-7 ]
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[ 89-83-8 ]
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2-isopropyl-5-methylphenyl 5-(4-chlorophenyl)furan-2-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
In benzene; for 5h;Reflux; |
General procedure: A mixture of 5-substituted phenyl-2-furancarboxylic acid (0.05 mol) and thionyl chloride (0.15 mol) was refluxed in anhydrous benzene for 3 h. The excess of thionyl chloride and the solvent were distilled off. The residues were dissolved in anhydrous benzene. The solution of 5-substituted phenyl-2-furancarbonyl chloride in anhydrous benzene was added into thymol or carvacrol. The mixture was stirred and refluxed for 5 h. After cooling, the solvent was evaporated off under reduced pressure, and the solid was recrystallized from ethanol to obtain the title compounds I and II. |
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[ 57753-80-7 ]
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[ 499-75-2 ]
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5-isopropyl-2-methylphenyl 5-(4-chlorophenyl)furan-2-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
In benzene; for 5h;Reflux; |
General procedure: A mixture of 5-substituted phenyl-2-furancarboxylic acid (0.05 mol) and thionyl chloride (0.15 mol) was refluxed in anhydrous benzene for 3 h. The excess of thionyl chloride and the solvent were distilled off. The residues were dissolved in anhydrous benzene. The solution of 5-substituted phenyl-2-furancarbonyl chloride in anhydrous benzene was added into thymol or carvacrol. The mixture was stirred and refluxed for 5 h. After cooling, the solvent was evaporated off under reduced pressure, and the solid was recrystallized from ethanol to obtain the title compounds I and II. |
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[ 57753-80-7 ]
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[ 92945-27-2 ]
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5-(4-chlorophenyl)-2-furoyl-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
58% |
With sodium hydroxide; In dichloromethane; water; at 20 - 50℃; |
With the thermometer in 50 ml three-mouth flask add 15mmol 5 - propyl - 1H - pyrazole -3 - ethyl formate with 10 ml dichloromethane, at room temperature by adding containing 15mmol sodium hydroxide 10% (wt.) of aqueous sodium hydroxide solution, control drop acceleration, keeping temperature at room temperature. After the completion of the pending, dropping containing 7.5mmol 5 - (4 - chlorophenyl) -2 - furan formyl chloride dichloromethane solution. Control dropping speed and, at the same time to make the adjustments. The completion of the dropping, slowly rising temperature to 50 C, in 50 C reaction 3 - 10h. After the reaction, filtration, to remove the precipitate, in order to remove the solvent and steaming and the filtrate, to obtain light yellow solid. Silica gel column (eluting agent is petroleum ether V/V ethyl acetate=3/1) to obtain the I - 1 compound, yield: 58% (I - 1). |
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[ 57753-80-7 ]
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[ 18686-82-3 ]
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C13H7ClN2O2S2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
68% |
With sodium hydroxide; In dichloromethane; at 50℃; |
Add 15 mmol to a 50 mL three-necked flask equipped with a thermometer1,3,4-thiadiazole-2-thiol(or 5-methyl-1,3,4-thiadiazole-2-thiol)With 10mL dichloromethane,A 10% (wt.) solution containing 15 mmol sodium hydroxide was added at room temperature to control the acceleration.Keep the temperature at room temperature.After completion, a dichloromethane solution containing 7.5 mmol of 5-(4-chlorophenyl)-2-furoyl chloride was added dropwise.Control the acceleration so that both are added at the same time.After the addition was completed, the temperature was gradually raised to 50C, and the reaction was conducted at 50C for 3 to 10 hours.After the reaction was completed, the precipitate was filtered off, the precipitate was removed, and the filtrate was evaporated to remove the solvent to give a pale yellow solid.The silica gel column (eluent V petroleum ether / V ethyl acetate = 3/1) was isolated to give the H-4 compound, yield: 68% |
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[ 57753-80-7 ]
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[ 29490-19-5 ]
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C14H9ClN2O2S2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
73% |
With sodium hydroxide; In dichloromethane; at 50℃; |
Add 15 mmol to a 50 mL three-necked flask equipped with a thermometer1,3,4-thiadiazole-2-thiol(or 5-methyl-1,3,4-thiadiazole-2-thiol)With 10mL dichloromethane,A 10% (wt.) solution containing 15 mmol sodium hydroxide was added at room temperature to control the acceleration.Keep the temperature at room temperature.After completion, a dichloromethane solution containing 7.5 mmol of 5-(4-chlorophenyl)-2-furoyl chloride was added dropwise.Control the acceleration so that both are added at the same time.After the addition was completed, the temperature was gradually raised to 50C, and the reaction was conducted at 50C for 3 to 10 hours.After the reaction was completed, the precipitate was filtered off, the precipitate was removed, and the filtrate was evaporated to remove the solvent to give a pale yellow solid.The silica gel column (eluent V petroleum ether / V ethyl acetate = 3/1) was isolated to give the H-4 compound, yield: 68%, Alternatively, the H-23 compound was isolated in a yield of 73%. |
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[ 635-46-1 ]
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[ 57753-80-7 ]
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[5-(4-chlorophenyl)-2-furanyl](3,4-dihydroquinolin-1(2H)-yl)-methanone
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
90.1% |
In dichloromethane; for 4h;Reflux; |
General procedure: A mixture of 5-substituted phenyl-2-furancarboxylic acid 2 (100mmol) and thionyl chloride (500mmol) was refluxed in anhydrous benzene for 3.5h. The excess of thionyl chloride and the solvent were distilled off, and the residue was dissolved in anhydrous dichloromethane. The solution of 5-substituted phenyl-2-furancarboxylic chloride in anhydrous dichloromethane was added into tetrahydroquinoline (110mmol). The mixture was stirred and refluxed for 4h. After cooling, the solvent was evaporated off under reduced pressure, and the solid was recrystallized from ethanol to obtain compounds 3a-3o. |
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[ 67-51-6 ]
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[ 57753-80-7 ]
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(5-(4-chlorophenyl)furan-2-yl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
73% |
With sodium hydroxide; In dichloromethane; water; at 50℃; |
Into a 50mL three-neck flask which is equipped with a thermometer, add 15mmol 3,5-dimethylpyrazole and 10mL dichloromethane, under room temperature added the drops of 10% (wt.) aqueous solution of sodium hydroxide containing 15mmol of sodium hydroxide, the drop rate is controlled at one drop per second, keeping the temperature at room temperature. When the sodium hydroxide solution is added drop-wise after that add the drops of 10mL solution of dichloromethane containing 7.5mmol of <strong>[57753-80-7]5-(4-chlorophenyl)-2-furoyl chloride</strong>, the drop rate is controlled at one drop per second. After the addition has been completed, the temperature is gradually raised at 50C, and the reaction is conducted at 50C for 3-10 hours. After the reaction is complete, it is filtered, the precipitate is removed, and the filtrate is spinned to remove the solvent, and then obtained light yellow solid. Separation with silica gel column (eluent: petroleum ether/ethyl acetate V/V = 5/l) obtained 1-3 compounds, yield: 73%. |
- 85
-
[ 57753-80-7 ]
-
tert-butyl 4-(2-chloro-4-(piperazin-1-ylmethyl)phenoxy)piperidine-1-carboxylate
[ No CAS ]
-
C32H37Cl2N3O5
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With triethylamine; In dichloromethane; at 20℃; |
General procedure: To a solution of 5-(3,4-difluorophenyl)furan-2-carboxylic acid (40 mg, 0.18 mmol) was added thionyl chloride (0.02 ml, 0.9 mmol) in 1,2-dichloroethane (1 mL), the reaction mixture were stirred for 30 min. After evaporating solvent, tert-butyl 4-(2-chloro-4-(piperazin-1-ylmethyl)phenoxy)piperidine-1-carboxylate 7 (82 mg, 0.20 mmol) and triethylamine (0.075 ml, 0.54 mmol) added crude acid chloride in dichloromethane. After being stirred at room temperature for 2 h, the mixture was diluted with water (30 mL), and extracted with dichloromethane (30 mL x 2). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo, giving a residue that was subjected to column chromatography on silica gel (3% MeOH/CH2Cl2) to afford 98 mg (89%) of the boc-protected compound. |
- 86
-
[ 57753-80-7 ]
-
tert-butyl 4-(2-chloro-4-(piperazin-1-ylmethyl)phenoxy)piperidine-1-carboxylate
[ No CAS ]
-
(4-(3-chloro-4-(piperidin-4-yloxy)benzyl)piperazin-1-yl)(5-(4-chlorophenyl)furan-2-yl)methanone
[ No CAS ]
- 87
-
[ 1679-18-1 ]
-
[ 57753-80-7 ]
- 88
-
[ 2527-99-3 ]
-
[ 57753-80-7 ]