Category: 53911-68-5

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The solution of commercial 3,4-diaminobenzophenone (0.43 g) and 3-(4-chlorophenyl)glutaric anhydride (0.45 g) in 1,4-dioxane (3 ml) was stirred under reflux for 0.5 h. 4M HCl in 1,4-dioxane (3 ml) was added and the solution is further heated to reflux for 2.5 h. After cooling to rt the precipitate is collected by suction filtration and washed with 1,4-dioxane and diethyl ether. The crude is recrystallised from acetic acid to give 4-(5-benzoyl-2-benzimidazolyl)-3-(4-chlorophenyl)butanoic acid HCl (0.64 g) as light brown solid.1H-NMR (500 MHz, DMSO-d6)): delta (ppm)=2.74 (dd, J=16.2, 8.6 Hz, 1H), 2.85 (dd, J=16.2, 6.1 Hz, 1H), 3.50 (dd, J=15.0, 9.1 Hz, 1H), 3.60 (dd, J=15.0, 6.9 Hz, 1H), 3.91 (m, 1H), 7.32 (d, J=8.5 Hz, 2H), 7.39 (d, J=8.5 Hz, 2H), 7.58 (t, J=7.6 Hz, 2H), 7.70 (t, J=7.4 Hz, 1H), 7.75 (dd, J=8.3, 1.3 Hz, 2H), 7.83 (dd, J=8.6, 1.5 Hz, 1H), 7.86 (d, J=8.6 Hz, 1H), 8.01 (d, J=1.4 Hz, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=32.83 (CH2), 39.17 (CH), 39.67 (CH2), 113.91 (CH), 115.78 (CH), 126.51 (CH), 128.37 (2CH), 128.52 (2CH), 129.19 (2CH), 129.54 (2CH), 131.02 (C), 131.46 (C), 132.70 (CH), 133.79 (C), 133.95 (C), 136.90 (C), 140.75 (C), 154.47 (C), 172.14 (CO), 194.71 (CO)., 53911-68-5

53911-68-5 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione 104639, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 3-(4-chlorophenyl)glutaric anhydride (0.5 g) and commercial 2-amino- 4-chlorothiophenol (0.37 g) is dissolved in boiling dichloromethane (3 ml). The solution is stirred overnight at rt. The precipitate is isolated by suction filtration, washed with dichloromethane, and dried in vacuo. The crude product is recrystallised from acetone to give 0.3 g of 4-(5-chloro-2-benzothiazolyl)-3-(4- chlorophenyl)butanoic acid as colourless crystals.1H-NMR (500 MHz, DMSOd6): delta (ppm) = 2.08 (S, 3H), 2.65 (dd, J = 16.0, 8.6 Hz,IH), 2.79 (dd, J = 16.0, 6.2 Hz, IH), 3.45 (dd, J = 14.8, 9.3 Hz, IH), 3.53 (dd, J = 14.8, 5.9 Hz, IH), 3.63 (m, IH), 7.29 (d, J = 8.7 Hz, 2H), 7.33 (d, J = 8.7 Hz, 2H),7.42 (dd, J = 8.6, 2.0 Hz, IH), 7.99 (d, J = 2.0 Hz, IH), 8.02 (d, J = 8.6 Hz, IH),12.17 (br s, IH).13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 39.27 (CH2), 40.02 (CH2),41.17 (CH), 121.59 (CH), 123.42 (CH), 124.84 (CH), 128.11 (2 CH), 129.54 (2 CH), 130.70 (C), 131.12 (C), 133.35 (C), 141.45 (C), 153.38 (C), 171.82 (C),172.42 (CO).MS ( + ESI): m/z = 366 (M + H)., 53911-68-5

53911-68-5 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione 104639, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

53911-68-5,53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The solution of commercial 4-nitro-l,2-phenylenediamine (0.31 g) and 3-(4- chlorophenyl)glutaric anhydride (0.45 g) in 1,4-dioxane (3 ml) was stirred under reflux for 0.75 h. 4M HCI in 1,4-dioxane (3 ml) was added and the solution is further heated to reflux for 1 h. After cooling to rt the precipitate is collected by suction filtration and washed with 1,4-dioxane and diethyl ether. The crude is recrystallised from acetic acid to give 4-(5-benzoyl-2-benzimidazolyl)-3-(4- chlorophenyl)butanoic acid HCI (0.59 g) as beige coloured solid. 1H-NMR (500 MHz, DMSO-d6)): delta (ppm) = 2.72 (dd, J = 16.2, 8.7 Hz, IH), 2.84(dd, J = 16.2, 6.1 Hz, IH), 3.41 (dd, J = 14.9, 8.9 Hz, IH), 3.52 (dd, J = 14.9, 7.0 Hz, IH), 3.85 (m, IH), 7.30 (d, J = 8.5 Hz, 2H), 7.36 (d, J = 8.5 Hz, 2H), 7.85 (d, J = 9.0 Hz, IH), 8.23 (dd, J = 9.0, 2.2 Hz, IH), 8.51 (d, J = 2.1 Hz, IH). 13C-NMR and DEPT (125 MHz, DMSO-d6) : delta (ppm) = 33.46 (CH2), 39.28 (CH), 39.64 (CH2), 110.68 (CH), 114.50 (CH), 119.70 (CH), 128.31 (2 CH), 129.19 (2 CH), 131.36 (C), 132.76 (C), 136.93 (C), 140.97 (C), 144.01 (C), 156.90 (C), 172.23 (CO).

The synthetic route of 53911-68-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.,53911-68-5

The solution of 4-chloro-1,2-phenylenediamine (2.85 g) and 3-(4-chlorophenyl)-glutaric anhydride (4.49 g) in 1,4-dioxane (7 ml) was stirred at rt for 1 h. The precipitate is collected by suction filtration, washed with 1,4-dioxane, and dried in vacuo to provide a mixture of regioisomeric amides (5.37 g) as beige coloured solid.This solid is dissolved in acetic acid (10 ml) with heating. Conc. HCl (4 ml) is added and the resulting solution is heated to reflux for 2 h. Then all volatiles are removed at the water aspirator and the still hot residue is suspended in acetone (20 ml). The suspension is cooled to rt with stirring and the solid is isolated by filtration. After washings with acetone the off- white solid is dried in vacuo to yield the hydrochloride salt of 4-(5-chloro-2-benzimidazolyl)-3-(4-chlorophenyl)butanoic acid (4.66 g).1H-NMR (500 MHz, DMSO-d6): delta (ppm)=2.72 (dd, J=16.2, 8.6 Hz, 1H), 2.83 (dd, J=16.2, 6.2 Hz, 1H), 3.43 (dd, J=14.9, 9.2 Hz, 1H), 3.55 (dd, J=14.9, 6.9 Hz, 1H), 3.86 (m, 1H), 7.30 (d, J=8.5 Hz, 2H), 7.36 (d, J=8.5 Hz, 1H), 7.48 (dd, J=8.8, 1.9 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.81 (d, J=1.8 Hz, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=32.67 (CH2), 39.19 (CH), 39.60 (CH2), 113.55 (CH), 115.25 (CH), 125.51 (CH), 128.34 (2CH), 129.14 (2CH), 129.56 (C), 129.96 (C), 131.43 (C), 131.92 (C), 140.70 (C), 153.27 (C), 172.11 (CO). MS (+ESI): m/z=349 (M+H).

The synthetic route of 53911-68-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53911-68-5, Prepared by refluxing an equimolar mixture of 3-(4-chlorophenyl)glutaric anhydride and commercial 4-chloro-2-hydroxyaniline in dichloromethane for 0.5 h. After cooling to rt the precipitated product is isolated by suction filtration, washed, and dried to provide 90% of Lambda/-(2-hydroxy-4-chlorophenyl)-3-(4-chlorophenyl)glutaramic acid as light red crystals.

The synthetic route of 53911-68-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53911-68-5, The solution of 3-(4-chlorophenyl)glutaric anhydride (449 mg) and anthranilamide (272 mg) in toluene (8 ml) was heated to reflux for 4 h. After removal of the solvent the residue was dried in vacuo. The off- white solid was dissolved in 2M sodium hydroxide (3 ml) and stirred under reflux for 2 h. After cooling to room temperature acetic acid (0.5 ml) was added with stirring. The precipitate formed was isolated by suction filtration, washed, and dried in vacuo to give 3-(4-chlorophenyl)-4-(4-hydroxy-2-quinazolinyl)butanoic acid (0.57 g) as colourless solid.1H-NMR (500 MHz, DMSO-d6)): delta (ppm)=2.62 (dd, J=16.0, 9.3 Hz, 1H), 2.74 (dd, J=16.0, 5.6 Hz, 1H), 2.86 (dd, J=14.4, 7.7 Hz, 1H), 2.93 (dd, J=14.4, 7.8 Hz, 1H), 3.74 (m, 1H), 7.32 (m, 4H), 7.44 (dt, J=8.0, 1.1 Hz, 1H), 7.59 (d, J=8.0, 1H), 7.76 (dt, J=7.7, 1.6 Hz, 1H), 8.04 (dd, J=7.9, 1.2 Hz, 1H), 12.10 (s, br, 1H), 12.20 (s, br, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=38.82 (CH), 39.37 (CH2), 40.75 (CH), 120.70 (C), 125.56 (CH), 125.98 (CH), 126.75 (CH), 128.07 (CH), 129.33 (CH), 130.90 (C), 134.19 (C), 142.22 (C), 148.59 (C), 155.17 (C), 161.59 (CO), 172.55 (CO).

The synthetic route of 53911-68-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Commercial 4-bromo-1,2-phenylenediamine (561 mg) and 3-(4-chlorophenyl)-glutaric anhydride (674 mg) were dissolved in THF (1 ml) with heating. The dark solution was stirred at rt for 1 h. Then the solution was decolourised with activated carbon and filtered. The filtrate was concentrated and the solid residue dried in vacuo. The solid was dissolved in a mixture of acetic acid (4 ml) and conc. HCl (2 ml) and stirred under reflux for 3 h. All volatiles were removed at the water aspirator and the residue was recrystallised from ethanol /EtOAc 1:3 to give a crude (0.47 g). The impure crude was again refluxed with acetic acid /conc. HCl 2:1 for 1 h to leave after concentration and acetone trituration 4-(5-bromo-2-benzimidazolyl)-3-(4-chlorophenyl)butanoic acid?HCl (0.3 g) as light greyish solid.1H-NMR (500 MHz, DMSO-d6): delta (ppm)=2.72 (dd, J=16.2, 8.6 Hz, 1H), 2.83 (dd, J=16.3, 8.2 Hz, 1H), 3.43 (dd, J=14.9, 9.2 Hz, 1H), 3.55 (dd, J=14.9, 6.9 Hz, 1H), 3.85 (m, 1H), 7.30 (d, J=8.5 Hz, 2H), 7.35 (d, J=8.5 Hz, 1H), 7.60 (dd, J=8.7, 1.7 Hz, 1H), 7.67 (d, J=8.7 Hz, 1H), 7.94 (d, J=1.7 Hz, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=32.66 (CH2), 39.19 (CH), 39.60 (CH2), 115.57 (CH), 116.42 (CH), 117.34 (C), 128.14 (CH), 128.34 (2CH), 129.14 (2CH), 130.26 (C), 131.44 (C), 132.32 (C), 140.69 (C), 153.07 (C), 172.12 (CO).MS (+ESI): m/z=393 (M+H)., 53911-68-5

As the paragraph descriping shows that 53911-68-5 is playing an increasingly important role.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics