Day: November 18, 2020

#REF!

Example-20: Preparation of (R)-4-phenyI-3-propionyIoxazolidin-2-one (Formula B-I) ( )-4-phenyloxazolidin-2-one (100 gm) and dimethylaminopyridine (10 gm) were added to a mixture of propionic acid (50 gm) and toluene (400 ml) at 25-30C. Cooled the reaction mixture to 0-5C, dicyclohexylcarbodiimide (151.5 gm) was slowly added and stirred the reaction mixture for 1 hr at the same temperature. Slowly raised the temperature of the reaction mixture to 25-30C and stirred for 14 hrs at the same temperature. Filtered the reaction mixture, aqueous hydrochloric acid solution was added to the filtrate and stirred the reaction mixture for 20 min at the same temperature. Both the organic and aqueous layers were separated and washed the organic layer with aqueous HC1 solution followed by with aqueous sodium bicarbonate solution and then with aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure and co- distilled with cyclohexane under reduced pressure. Cyclohexane (200 ml) was added to the obtained solid at 55-60C and stirred for 15 min at the same temperature. Cooled the reaction mixture to 25-30C and stirred for 40 min at the same temperature. Filtered the solid, washed with cyclohexane and dried to get the title compound. Yield: 124.0 gm. M.R: 81-82C., 90319-52-1

Other significant industrial processes that involve the use of heterogeneous catalysts include the preparation of sulfuric acid, the preparation of ammonia, the oxidation of ammonia to nitric acid, and the synthesis of methanol. 90319-52-1, if you are interested, you can browse my other articles.

Reference£º
Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; VENKAT REDDY, Ghojala; WO2015/87351; (2015); A2;,
Oxazolidine – Wikipedia
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A heterogeneous catalyst is a catalyst that is present in a different phase than the reactants. Such catalysts generally function by furnishing an active surface upon which a reaction can occur. 2346-26-1, name is Oxazolidine-2,4-dione, introduce a new downstream synthesis route as follows., 2346-26-1

WORKING EXAMPLE 1 A mixture of 3-methoxy-4-(2-phenyl-4-oxazolylmethoxy)cinnamaldehyde (5.5 g), 2,4-oxazolidinedione (6.7 g), piperidine (1.4 g) and acetic acid (120 ml) was stirred for three days under reflux. The reaction mixture was cooled, and resulting crystalline precipitate was collected by filtration, which was washed with water, ethanol and isopropyl ether, successively to give 5-[3-methoxy-4-(2-phenyl-4-oxazolylmethoxy)cinnamylidene]-2,4-oxazolidinedione (2.9 g, 43%), which was recrystallized from chloroform-methanol to afford yellow needles, m.p.227-228 C.

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Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5932601; (1999); A;,
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139009-66-8, The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism. If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 139009-66-8, name is (S)-N-Boc-2,2-dimethyloxazolidine-4-carboxylic Acid. A new synthetic method of this compound is introduced below.

Isobutyl chloroformate (2.51 g; 2.40 mL; 18.36 mmol) and triethylamine (2.25 g; 3.10 mL; 22.24 mmol) were added to a cold (0 C) solution of aminoacetal 2c from the previous step (?3.35 g; 14.27 mmol) in dichloromethane (11 mL) under an argon atmosphere. The reaction mixture was vigorously stirred for 30 min at 0 C, then ethanethiol (2.01 g; 2.40 mL; 32.41 mmol) and triethylamine (2.25 g; 3.10 mL; 22.24 mmol) were added. The resulting solution was stirred for 30 min at 0 C and 45 min at rt. The reaction mixture was diluted with dichloromethane (25 mL), washed with water (40 mL) and brine (30 mL), dried over anhydrous MgSO4, concentrated under reduced pressure and purified by distillation under reduced pressure (bp 110 C/0.3 mmHg) to give 2.19 g (53% over three steps) of thioester 5, as white crystals.

In every case, we must determine the overall rate law from experimental data and deduce the mechanism from the rate law (and sometimes from other data). you can also browse my other articles about 139009-66-8 if you are interested.

Reference£º
Article; Trajkovic, Milos; Ferjancic, Zorana; Saicic, Radomir N.; Tetrahedron Asymmetry; vol. 23; 8; (2012); p. 602 – 604;,
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An elementary termolecular reaction involves the simultaneous collision of three atoms, molecules, or ions.(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one, cas is 145589-03-3. Here is a downstream synthesis route of the compound 145589-03-3. 145589-03-3

Intermediate 15: [(R)-4-BENZVL-3- (2-HYDROXYMETHYL-3-METHVL-BUTANOYL)-OXAZOLIDINONE] [4-BENZYL-3- (3-METHYLBUTANOYL)-OXAZOLIDINONE] (14) * (26. 1g, 0.1mol) was stirred in dry [DICHLOROMETHANE (400ML)] at [0C] under nitrogen as titanium tetrachloride (1. 0M solution in dichloromethane, 105ml, 0. [105MOL)] was added and the mixture, which contained a yellow precipitate, was stirred a further 15 minutes then [DIISOPROPYLETHYLAMINE (19ML, 0. 11MOL)] was added dropwise, maintaining the temperature below [5C.] The resulting purple solution was stirred for 75 minutes then 1,3, 5-trioxane (9.9g, [0.] 11mol) in [DICHLOROMETHANE] (60ml) was added, and after a further 10 minutes, titanium tetrachloride (1. [OM] in DCM, 105ml, 0. [105MOL)] was added. The mixture was stirred for 2.5 hours at [0C] then quenched by the addition of saturated ammonium chloride (500ml). Water (100ml) and [DICHLOROMETHANE] [(100ML)] were added, the aqueous phase extracted with a further 2 x [100ML DICHLOROMETHANE,] the combined organics dried over [NA2SO4] and evaporated. Recrystallisation from 30% [DICHLOROMETHANE/PETROLEUM] gave 18.7g (64%) of the title compound as a white solid. LCMS RT=2.94minutes [MH+ 292], 145589-03-3

Other significant industrial processes that involve the use of heterogeneous catalysts include the preparation of sulfuric acid, the preparation of ammonia, the oxidation of ammonia to nitric acid, and the synthesis of methanol. 145589-03-3, if you are interested, you can browse my other articles.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2003/104200; (2003); A1;,
Oxazolidine – Wikipedia
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We know that the rate of many reactions can be accelerated by catalysts. A catalyst speeds up the rate of a reaction by lowering the activation energy; in addition, the catalyst is regenerated in the process. 2346-26-1, name is Oxazolidine-2,4-dione,below Introduce a new synthetic route., 2346-26-1

Step 2 3-(2-((3R,4aR,6aS,7R,10bR)-3-(3,4-difluorophenyl)-6a,10b-dimethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethyl)oxazolidine-2,4-dione (4aR,6aS,7R,10bR)-7-(2-bromoethyl)-3-(3,4-difluorophenyl)-6a,10b-dimethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin (150 mg, 0.33 mmol) and potassium carbonate (91 mg, 0.66 mmol) were dissolved in N,N-dimethylformamide (2 mL), added with oxazolidine-2,4-dione (67 mg, 0.66 mmol) and stirred at 80 C. for 1.5 hours. The reaction solution was quenched with water and extracted with dichloromethane (50 mL*3). The organic layer was washed with saturated brine and water, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure and separated on a thin layer chromatography plate to give 3-(2-((3R,4aR,6aS,7R,10bR)-3-(3,4-difluorophenyl)-6a,10b-dimethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethyl)oxazolidine-2,4-dione 215 (70 mg, yield: 44.7%). 1H NMR (400 MHz, CDCl3) 7.36-7.31 (m, 1H), 7.19-7.12 (m, 2H), 5.70 (s, 1H), 4.96 (s, 1H), 4.78 (s, 1H), 4.68 (s, 1H), 4.22 (d, J=11.6 Hz, 1H), 3.68-3.45 (m, 4H), 2.48-1.78 (m, 6H), 1.69 (s, 3H), 1.28-1.25 (m, 3H), 0.79 (s, 3H)., 2346-26-1

Any one of these steps may be slow and thus may serve as the rate determining step. In general, however, in the presence of the catalyst, the overall rate of the reaction is faster than it would be if the reactants were in the gas or liquid phase.

Reference£º
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

#REF!

To an ice cold solution of commercially available 1 (35 g, 135 mmol) in THF/MeOH (500 mL (95:5)), was added LiBH4 (5.9 g, 271 mmol) portionwise and the suspension was stirred for 2 h at RT. The reaction mixture was cooled and quenched with ice. Solvent was removed under reduced pressure, and water was added. The aqueous layer was extracted with EtOAc, concentrated and chromatographed (EtOAc:hexanes, 3:7) to yield 2 (23 g, 74 % yield)., 108149-60-6

Other significant industrial processes that involve the use of heterogeneous catalysts include the preparation of sulfuric acid, the preparation of ammonia, the oxidation of ammonia to nitric acid, and the synthesis of methanol. 108149-60-6, if you are interested, you can browse my other articles.

Reference£º
Patent; EXELIXIS, INC.; XU, Wei; (170 pag.)WO2017/4609; (2017); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

An elementary termolecular reaction involves the simultaneous collision of three atoms, molecules, or ions.(R)-4-Phenyloxazolidin-2-one, cas is 90319-52-1. Here is a downstream synthesis route of the compound 90319-52-1. 90319-52-1

General procedure: Procedure 1: To a solution of alkyne (9.80 mmol, 1.0 equiv) in acetone (10 mL) was added NBS (10.78 mmol, 1.1 equiv) and AgNO3 (0.98 mmol, 0.1 equiv). The resulting solution was stirred under nitrogen at room temperature for 4 h. After removing excess acetone the reaction was quenched with water and extracted with petroleum ether three times, dried over MgSO4, and concentrated under reduced pressure. The residue was eluted through a short silica column (petroleum ether) to obtain the bromoalkyne. To a dried flask was added 2-oxazolidone (4.8 mmol, 1.2 equiv), CuSO4¡¤5H2O (100 mg, 0.4 mmol, 0.1 equiv), 1,10-phenanthroline (144 mg, 0.8 mmol, 0.2 equiv) and K2CO3 (1.38 g, 10.0 mmol, 2.5 equiv), bromoalkyne (4.0 mmol, 1.0 equiv) and this mixture was subsequently treated with anhydrous toluene (10 mL). The flask was charged with nitrogen, and the solution was heated at 80 ¡ãC overnight. After completion, the crude reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. Purification of the crude residue using silica gel flash column chromatography yielded the pure ynamides., 90319-52-1

Other significant industrial processes that involve the use of heterogeneous catalysts include the preparation of sulfuric acid, the preparation of ammonia, the oxidation of ammonia to nitric acid, and the synthesis of methanol. 90319-52-1, if you are interested, you can browse my other articles.

Reference£º
Article; Wang, Wan-Shu; Chen, Ping; Tang, Yu; Tetrahedron; vol. 73; 19; (2017); p. 2731 – 2739;,
Oxazolidine – Wikipedia
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2346-26-1, The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism. If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 2346-26-1, name is Oxazolidine-2,4-dione. A new synthetic method of this compound is introduced below.

5.2. 3-{[1-(1-Isoquinolyl)-4-piperidyl]methyl}-1,3-oxazolidine-2,4-dione A solution of 2.01 g (9.95 mmol) of diisopropyl azodicarboxylate (DIAD) in 5 ml of tetrahydrofuran is added dropwise, under an inert atmosphere, to a solution of 2.4 g (9.95 mmol) of [1-(1-isoquinolyl)-4-piperidyl]methanol, prepared in step 5.1, 2.87 g (10.94 mmol) of triphenylphosphine and 1.21 g (11.93 mmol) of 1,3-oxazolidine-2,4-dione in 40 ml of tetrahydrofuran, cooled to about -10 C., the temperature of the reaction medium being maintained throughout between -10 C. and 0 C. Stirring is then continued at 0 C. for 1 hour and then at 25 C. for 18 hours. The mixture is concentrated under reduced pressure and the residue is taken up in dichloromethane and 10 ml of aqueous 5% sodium hydroxide solution. The aqueous phase is separated out and then extracted twice with dichloromethane. The organic phases are combined and washed successively with aqueous hydrochloric acid solution (1N) and then with saturated aqueous sodium hydrogen carbonate solution and with saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulfate and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by chromatography on silica gel, eluding with a 99/1/0.1 and then 98/2/0.2 mixture of dichloromethane, methanol and 28% aqueous ammonia. 3.57 g of oxazolidinedione are thus obtained in the form of an orange paste., 2346-26-1

There are, however, a few established termolecular elementary reactions. The reaction of nitric oxide with oxygen appears to involve termolecular steps. you can also browse my other articles about2346-26-1

Reference£º
Patent; Sanofi-Aventis; US2006/89344; (2006); A1;,
Oxazolidine – Wikipedia
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7517-99-9, The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism. If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 7517-99-9, name is 5-(Hydroxymethyl)oxazolidin-2-one. A new synthetic method of this compound is introduced below.

7517-99-9, General procedure: A Schlenk tube was charged with aryl bromide(1 mmol), oxazolidone(1.2 mmol), N,N-dimethylglycine(10.3mg, 0.1 mmol), recrystallized CuI(9.5mg, 0.05 mmol) and K2CO3(276mg, 2 mmol). The tube was evacuated and backfilled with argon(3 times) before dry DMF(0.5 ml) was added. The reaction mixture was stirred at 120 C until the corresponding aryl bromidewas completely consumed as monitored by TLC. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with H2O and brine, and dried by Na2SO4. Removal of solvent in vacuo and purified by column chromatography on silica gel to provide the desired product.

In every case, we must determine the overall rate law from experimental data and deduce the mechanism from the rate law (and sometimes from other data). you can also browse my other articles about 7517-99-9 if you are interested.

Reference£º
Article; Li, Jiaojiao; Zhang, Yihua; Jiang, Yongwen; Ma, Dawei; Tetrahedron Letters; vol. 53; 31; (2012); p. 3981 – 3983;,
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A heterogeneous catalyst is a catalyst that is present in a different phase than the reactants. Such catalysts generally function by furnishing an active surface upon which a reaction can occur. 95530-58-8, name is (R)-4-Isopropyloxazolidin-2-one, introduce a new downstream synthesis route as follows., 95530-58-8

95530-58-8, General procedure: n-BuLi (2.89M, 7.12mL, 20.6mmol) was added dropwise over 15min to a cold (-78C), stirred solution of (R)-4-isopropyloxazolidin-2-one 3 (2.5g, 19.6mmol) in dry THF (80mL), and the mixture was stirred at -78C for 30min. Octanoyl chloride (3.67mL, 21.5mmol) was then added dropwise, and the resulting mixture was stirred at -78C for 20min, then warmed to -10C for 2h. The mixture was quenched with 1M aqueous K2CO3 (100mL) and warmed to room temperature. The crude products were extracted with hexanes (2¡Á100mL), and the combined hexane extracts were washed with water and brine, dried, and concentrated. The residue was purified by flash chromatography on silica gel (50g). Elution with hexane/EtOAc (9:1) afforded 4.93g (19.3mmol, 98%) of (R)- 4 as a colorless oil, numax (neat): 2958 (m), 2927 (s), 2854 (m), 1777 (s), 1699 (s), 1487 (w), 1465 (m), 1384 (s), 1301 (m), 1269 (w), 1232 (m), 1204 (s), 1120 (w), 1091 (w), 1059 (m), 1020 (m), 971 (w), 773 (m), 723 (w), 708 (w); ?H (CDCl3): 0.78 (3H, m), 0.82 (6H, d, J=6.2Hz), 1.18 (6H, m), 1.55 (2H, m), 2.28 (1H, m), 2.74 (1H, pseudoquintet, J=6.2Hz), 2.89 (1H, pseudoquintet, J=6.4Hz), 4.11 (1H, dd, J=16, 4Hz), 4.18 (1H, pseudotriplet, J=8.4Hz), 4.34 (1H, m); ?C (CDCl3): 14.0, 14.9, 18.0, 23.0, 24.9, 28.2, 29.3, 31.9, 35.8, 58.5, 63.5, 154, 173.8; GC-MS [column: DB-5MS, 5% phenylmethylsiloxane, 30m¡Á0.25mm id; carrier gas, He; temp: 50-280C (10C/min)]: tR: 19.43min (100%); MS of 4 (70eV, EI); m/z: 255 (1, M+), 212 (2), 184 (5), 171 (8), 142 (1), 127 (17), 109 (3), 85 (9), 71 (8), 57 (42), 41 (47).

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Reference£º
Article; Bello, Jan E.; Millar, Jocelyn G.; Tetrahedron Asymmetry; vol. 24; 13-14; (2013); p. 822 – 826;,
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