Dioxole related

144690-92-6, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”144690-92-6

Into a 1000 mL four-necked flask equipped with a two-piece stirring blade having a diameter of 10 cm,50 g of trityl olmesartan medoxomil, 225 ml of acetic acid and 75 ml of water were added and stirred at 40 C. for 2 hours to carry out deprotection reaction.Subsequently, the reaction solution was cooled to 20 C. and stirred at 20 C. for 1 hour, and the precipitated triphenylmethanol was removed by vacuum filtration,To the obtained filtrate were added 250 ml of 10% sodium hydrogen carbonate and 500 ml of ethyl acetate, followed by vigorous stirring, and the aqueous layer was separated to obtain an organic layer containing olmesartan medoxomil.200 ml of ethyl acetate was distilled off from the organic layer, and the mixture was stirred at 20 to 30 C. for 1 hour. The precipitated solid was collected by filtration under reduced pressure as a wet body.The obtained wet body was dried at 40 C. for 14 hours to obtain 30 g of crystals of olmesartan medexomil (purity: 99.54%)., 144690-92-6

As the rapid development of chemical substances, we look forward to future research findings about 144690-92-6

Reference£º
Patent; TOKUYAMA CORPORATION; MORI, HIROYUKI; TANAKA, KENJI; (11 pag.)JP2015/74608; (2015); A;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

Triphenyl methyl olmesartan, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”144690-92-6

Trityl olmesartan medoxomil (8 g, 10 mmol) is added to a mixture of acetone (35 ml) and water (10 ml). To the resulting suspension 37 % aqueous hydrochloric acid (2.5 ml, 30 mmol) is added. The mixture is then stirred at room temperature for 4 h. Water (130 ml) is added and the mixture is stirred for additional 30 minutes. The precipitated triphenylmethanol is filtered off. The filtrate is concentrated in vacuum at 40 C to 100 ml, and then stirred vigorously for 1 h at room temperature and then additional 30 minutes at 0 C. The precipitate is filtered to give 4.7 g of olmesartan medoxomil hydrochloride Form A (98.3 % area)

The chemical industry reduces the impact on the environment during synthesis, Triphenyl methyl olmesartan, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; LEK Pharmaceuticals d.d.; EP2022790; (2009); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.37830-90-3, 4,5-Dimethyl-1,3-dioxol-2-one it is a common compound, a new synthetic route is introduced below.37830-90-3

Compound 20 was prepared following the steps disclosed in the literature (Sakamoto er a/., Chem. Pharm. Bull, 1984, 32, 2241).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 4,5-Dimethyl-1,3-dioxol-2-one reaction routes.

Reference£º
Patent; ANCHEN LABORATORIES, INC; WO2009/118580; (2009); A2;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”80841-78-7

130 ml of N,N-dimethylacetamide, 14.0 g (20 mmol) of ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylate and 2.2 g (16 mmol) of KOH were charged into reaction vessel at room temperature under inert atmosphere. The mixture was stirred at room temperature for 2 h, and then the sample of reaction mixture was analysed (HPLC; starting material 0.2 %, hydrolysed starting material 98.11 %). Then 3.0 g (2.2 mmol) of potassium carbonate powder and 1.4 g (8.4 mmol) of potassium iodide were added. The reaction mixture was cooled to 0 C and 5.0 g (33 mmol) of 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one was added at 0 to 5C. After the addition, the reaction mixture was warmed to 40-45 C within one hour, then the mixture was stirred at this temperature for 2h. The sample of reaction mixture was analysed (HPLC; tritylolmesartan medoxomil 97.22 %, 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylate 0.09 %). The mixture was cooled to 10 to 20 C and then 250 ml of ethyl acetate was added. The mixture was cooled again to 5-10 C and then 200 ml of 10 % NaCl was added slowly. The temperature should not be higher than 25 C during the addition. The phases were mixed separated and organic phase was washed with 100 ml of 10 % NaCl (2*) and dried over anhydrous sodium sulphate. After the filtration filtrate was evaporated under reduced pressure at temperature under 45C to oily residue. To the residue 30 ml of acetonitrile was added at temperature not more than 45C. The mixture was stirred at this temperature for 10 minutes then was cooled to 20 to 25C and stirred at this temperature for 0.5 h and after that 3h at 0 to 5C. The suspension was filtered, the cake washed with cold acetonitrile and dried at 40 to 50C. Yield: 17.0 g (94%) HPLC: 99.72 % of the product, all impurities are under 0.1%. IR: 3408, 1818, 1805, 1741, 1681, 1529, 1147, 1003, 699 XRD:

The chemical industry reduces the impact on the environment during synthesis, 4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Krka Tovarna Zdravil, D.D., Novo Mesto; EP2334668; (2011); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

144690-92-6, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”144690-92-6

Example 2 Olmesartan medoxomil of formula I20 g of the starting compound of formula III were stirred up in 75 ml of acetic acid and after stirring for 10 minutes 30 ml of water were added dropwise during 5 minutes. Then, the suspension was put in a 50C bath and stirred for 4 hours. Then 16 ml of water were added dropwise in 5 minutes, the mixture was taken out of the bath and after 5 minutes it was put in a cooling bath with the temperature of 10C. After 20 minutes the separated insoluble fraction, containing the side product trityl alcohol, was aspirated and washed with a mixture of 4 ml of AcOH + 2 ml of water. 40 ml of acetone and then 70 ml of water were added to the filtrate at 30C, the separated product was aspirated and 1 1.5 g (82 %) of the product were obtained., 144690-92-6

As the rapid development of chemical substances, we look forward to future research findings about 144690-92-6

Reference£º
Patent; ZENTIVA, K. S.; STACH, Jan; JARRAH, Kamal; KRULIS, Radim; RADL, Stanislav; CERNY, Josef; WO2012/55380; (2012); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.37830-90-3, 4,5-Dimethyl-1,3-dioxol-2-one it is a common compound, a new synthetic route is introduced below.37830-90-3

(1) Synthesis of 4-bromomethyl-5-methyl-1,3-dioxolen-2-one[the compound of formula (III) in which X is a bromine atom]: 3.42 g of 4,5-dimethyl-1,3-dioxolen-2-one (synthesised in accordance with Tetrahedron Letters, (1972), pages 1701-1704) was dissolved in 150 ml of carbon tetrachloride, and 5.34 g of N-bromosuccinimide and a catalytic amount of alpha,alpha’-azobisisobutyronitrile were added. The mixture was heated under reflux for 15 minutes. The reaction mixture was concentrated to half of its volume and the resulting insoluble matter was removed by filtration. Concentrating the filtrate gave a syrupy residue. The residue was distilled under reduced pressure to give a fraction boiling at 115¡ã to 120¡ã C./5 mm Hg which was 4.2 g (yield 73percent) of the captioned compound., 37830-90-3

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 4,5-Dimethyl-1,3-dioxol-2-one reaction routes.

Reference£º
Patent; Kanebo Ltd.; US4455310; (1984); A;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.37830-90-3, 4,5-Dimethyl-1,3-dioxol-2-one it is a common compound, a new synthetic route is introduced below.37830-90-3

(1) 2.08 g of 4,5-dimethyl-1,3-dioxol-2-one was dissolved in 24 mL of benzene, to which 3.25 g of N-bromosuccinimide and 86 mg of 2,2′-azobis(isobutyronitrile) were added at room temperature, and this mixture was stirred for 30 minutes while heating it under reflux. The reaction mixture was cooled to room temperature, and consequently, a solution of 4-bromomethyl-5-methyl-1,3-dioxol-2-one in benzene was obtained.(2) 3.00 g of methyl 3-(5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-{[3-(methoxymethoxy)-1,2-benzisoxazol-6-yl]methoxy}phenyl) propanoate was dissolved in 15 mL of methanol and 15 mL of tetrahydrofuran, to which a solution of 1.08 g of potassium hydroxide in 4.5 mL of water was added, and this mixture was stirred for one hour at room temperature, and then the solvent was distilled out under reduced pressure. The resultant residue was dissolved in 40 mL of N,N-dimethylformamide, to which 3.60 g of potassium carbonate was added. Then, the benzene solution prepared in (1) was added thereto, and was stirred for one hour at room temperature. The reaction mixture was poured into a mixture of ethyl acetate and water, and adjusted to pH 7 with 6M hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; toluene:ethyl acetate=5:1] to yield 1.58 g of (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 3-(5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-{[3-(methoxymethoxy)-1,2-benzisoxazol-6-yl]methoxy}phenyl) propanoate as yellow oil. NMR(400MHz,CDCl3) delta value: 1.5-2.0(8H,m), 2.16(3H,s), 2.75(2H,t,J=7.6Hz), 3.10(2H,t,J=7.6Hz), 3.65(3H,s), 4.5-5.0(3H,m), 5.33(2H,s), 5.57(2H,s), 6.37(1H,dd,J=8.8,2.4Hz), 6.47(1H,d,J=2.4Hz), 6.95(1H,d,J=8.4Hz), 7.35(1H,dd,J=8.4,1.2Hz), 7.4-7.6(4H,m), 7.72(1H,d,J=8.0Hz), 12.67(1H,s).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 4,5-Dimethyl-1,3-dioxol-2-one reaction routes.

Reference£º
Patent; TOYAMA CHEMICAL CO., LTD.; Hirono, Shuichi; Shiozawa, Shunichi; EP1445249; (2004); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

144690-92-6, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”144690-92-6

The reaction flask was charged with 400 g of compound VII (0.50 mol) and 70% aqueous acetic acid solution of 3200 ml, Reaction was carried out at 50 C for 2 hours. After the completion of the reaction, the solvent was concentrated and concentrated, and ammonia was added to the residue.PH = 7, extracted with 1400 ml of ethyl acetate, the ethyl acetate layer was washed with water, and finally with anhydrous sodium sulfateDried; filtered, the filtrate was concentrated to dryness and the residue was recrystallized from ethanol to give the compound I pure product 256.1G, yield: 91.79%.

With the synthetic route has been constantly updated, we look forward to future research findings about Triphenyl methyl olmesartan,belong Dioxole compound

Reference£º
Patent; Hunan Ouya biological Co. Ltd.; Lin, kaizhao; (19 pag.)CN103304550; (2016); B;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”80841-78-7

To BIC (110 g, 1 eq) was added acetone (385 mL, 3.5 vol) at 25C – 30C, and the mixture was dissolved by stirring for 5 min. Sodium carbonate (20.85 g, 1.3 eq) and potassium iodide (0.25 g, 0.01) were added, and the mixture was stirred for 10 min. A solution of 4-chloromethyl-5-methyl-2-oxo-1,3-dioxolene (31.456 g, 1.4 eq) in acetone (165 mL, 1.5 vol) was added thereto. The reaction mixture was heated to 45C – 50C, and stirred at the same temperature for 12 hr. Using TLC (thin layer chromatography) (TLC eluent: 10% methanol/methylene chloride, detection method: UV), complete disappearance of BIC was confirmed. The reaction mixture was cooled to 25C – 30C. Then, the solvent contained in the reaction mixture was evaporated under reduced pressure at 40C – 45C. To the obtained residue were added 10% brine (550 mL, 5 vol) and toluene (550 mL, 5 vol). Furthermore, the mixture was adjusted to pH 7 – 8 by adding 5% hydrochloric acid (33 mL), stirred for 10 min, left standing for 5 min and partitioned. The aqueous layer was extracted with toluene (2×330 mL, 2×3 vol). The extracts were combined with the organic layer, 10% brine (550 mL, 5 vol) was added, and the mixture was stirred for 5 min, left standing for 45 min, partitioned, and concentrated under reduced pressure at 40C – 45C to give TOLM (110 g, 90%). [0306] To the obtained TOLM was added acetone (110 mL, 1 vol), and the mixture was stirred at 25C – 30C for 30 min. n-Heptane (440 mL, 4 vol) was added, and the mixture was cooled to 5C – 10C and stirred at 5C – 10C for 30 min, whereby precipitation of a solid was confirmed. The solid (80 g, 66%) was collected by filtration, and blast dried. To the obtained solid was added isopropyl alcohol (400 mL, 5 vol), and the mixture was heated to 50C – 55C and stirred at 50C – 55C for 1 hr. Then, the mixture was cooled to 25C – 30C, and stirred at 25C – 30C for 1 hr. The resulting solid was filtered and suction-filtered for 10 min to give TOLM (76 g, 62%).

The chemical industry reduces the impact on the environment during synthesis, 4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; API Corporation; SEKI, Masahiko; EP2891650; (2015); A1;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem

4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”80841-78-7

Toluene (180 L) is placed into a reactor and water (3.17 L) is added, followed by addition of ethyl-4-(1 -hydroxy-1 -methylethyl)-2-propylimidazole-5- carboxylate (18.0 Kg). The mass is stirred for about 10 minutes, heated to about 45C, and potassium carbonate (25.85 Kg) is added. The temperature of the mass is raised to about 65C and maintained for about 45 minutes. N-(triphenylmethyl)- 5-[4′-(bromomethyl)biphenyl-2-yl]tetrazole (48.9 Kg) and tetrabutylammonium bromide (4.82 Kg) are added at the same temperature and the mixture is stirred at 60-700C for 10 hours. Reaction completion is verified using thin layerchromatography (TLC). After the reaction is complete, the mass is washed with water (3*120 L) at about 500C. The mass is cooled to about 25C and toluene (468 L) and potassium tertiary-butoxide (12.6 Kg) is added, then the mass is maintained at the same temperature for about 1 hour. Water (0.85 L) is added and the mass is maintained at the same temperature for about 2 hours. Reaction completion is verified using TLC, then 5-methyl-2-oxo-(1 ,3-dioxolene-4-yl)methyl chloride (20 Kg), tetrabutylammonium bromide (4.82 Kg), and sodium carbonate (3.96 Kg) are added at 40-450C. The mass is stirred at about 55C for about 11 hours. After the reaction is complete, the mass is cooled to about 20C, water (540 L) is added and the pH is adjusted to about 6-7 by adding 10% aqueous HCI. The layers are separated. The aqueous layer is extracted with toluene (240 L). The organic layers are combined and washed with water (270 L). The solvent is distilled under reduced pressure. Acetone (189 L) is added to the residue and the mixture is heated to about 45C to produce a solution, then the solution is cooled to about 300C and maintained for about 20 minutes, followed by cooling to about 2C and maintaining for about 3 hours. The formed solid is filtered, washed with acetone (54 L), and dried for about 4 hours. The material obtained is re- crystallized from acetonitrile to yield 34.0 Kg of the title compound.

The chemical industry reduces the impact on the environment during synthesis, 4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; KOLLA, Naveen Kumar; MANNE, Nagaraju; NAREDLA, Anitha; SHINDE, Sachin Gulabrao; WO2011/14611; (2011); A2;,
1,3-Benzodioxole – Wikipedia
Dioxole | C3H4O2 – PubChem