Category: 16332-06-2

Nirmala, Muthukumaran published the artcileRuthenium(II) complexes incorporating salicylaldiminato-functionalized N-heterocyclic carbene ligands as efficient and versatile catalysts for hydration of organonitriles, Category: ethers-buliding-blocks, the publication is Inorganica Chimica Acta (2016), 134-144, database is CAplus.

Authors describe a new synthetic procedure for synthesis of ruthenium(II) complexes containing salicylaldiminato functionalized mixed N-heterocyclic carbene (NHC) ligand and phosphine co-ligand. The complexes (3a–3d) have been obtained in good to excellent yields by transmetalation from the corresponding Ag-NHC complexes (2a–2d) as carbene transfer reagents. All the [Ru-NHC] complexes have been characterized by elemental analyses, spectroscopic methods as well as ESI mass spectrometry. The ligands 1a–1d show their versatility by switching to be O,N,C-chelating in these ruthenium(II) complexes. The resulting complexes have been evaluated as potential catalysts for the selective hydration of nitriles to primary amides, and related amide bond forming reactions, in environmentally friendly medium. The reaction tolerated ether, hydroxyl, nitro, bromo, formyl, pyridyl, benzyl and alkyl functional groups. The catalyst was stable for weeks and could be recovered and reused more than six times without significant loss of activity.

Inorganica Chimica Acta published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Schmidtchen, Franz P. published the artcilePolyprenylpyridinols. Synthesis of piericidin analogs, Recommanded Product: 2-Methoxyacetamide, the publication is Journal of the American Chemical Society (1977), 99(21), 7014-19, database is CAplus and MEDLINE.

The piericidin A analogs I (n = 1, 2, 3, 9) and II were prepared for structure-activity studies on coenzyme Q inhibitors. To prepare the nucleus, 3-methoxyacetylamino-2-methylacrylonitrile was cyclized to a 4-amino-2-pyridone which Me₃O⁺ BF₄^– converted to the 4-amino-2,3-dimethoxypyridine. Bromination of the acylated amine formed the 6-bromo derivative in which the 4-amino group was then replaced by hydroxy and the latter blocked by conversion to its benzyl ether with a benzylisourea. Transmetalation now gave the 6-lithio compound which was coupled with various prenyl bromides, leading to introduction of all trans polyprenyl side chains. The final 4-pyridinols were formed on selective debenzylation with butyl mercaptide. All the polyprenylpyridinols inhibited coenzyme Q electron transport to some extent, with the farnesyl analog having the same activity as piericidin A.

Journal of the American Chemical Society published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Recommanded Product: 2-Methoxyacetamide.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Kumaresan, R. published the artcileSynthesis and evaluation of N,N-di-alkyl-2-methoxyacetamides for the separation of U(VI) and Pu(IV) from nitric acid medium, COA of Formula: C3H7NO2, the publication is Radiochimica Acta (2017), 105(9), 699-707, database is CAplus.

The homologs of N,N-di-alkyl-2-methoxyacetamides (DAMeOA) having three different alkyl chains varying from hexyl to decyl (C₆, C₈ and C₁₀) were synthesized and characterized by NMR and IR spectral analyses. Extraction behavior of U(VI) and Pu(IV) from nitric acid medium in a solution of 0.5 M of DAMeOA in n-dodecane (n-DD) was studied and the results were compared with those obtained using N,N-di-hexyloctanamide (DHOA) in n-dodecane. The effect of various parameters on the distribution ratio of U(VI) and Pu(IV) in DAMeOA was studied. The extraction of nitric acid increased with decrease in chain length of alkyl group attached to amidic nitrogen atom of DAMeOA and the conditional nitric acid extraction constant was determined The extraction of nitric acid in DAMeOA/n-DD resulted in the formation of third phase in organic phase and the third phase occurred early with DAMeOA having smaller alkyl chain length. In contrast to this, the distribution ratio (D) of U(VI) and Pu(IV) in DAMeOA/n-DD increased with increase in the concentration of nitric acid and with increase in the chain length of alkyl group attached to amidic nitrogen atom of DAMeOA. The stoichiometry of the metal – solvate was determined from the slope of extraction data. Quant. recovery of uranium and plutonium from the loaded organic phase was achieved using dilute nitric acid.

Radiochimica Acta published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, COA of Formula: C3H7NO2.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Breno, Kerry L. published the artcileAqueous Phase Organometallic Catalysis Using (MeCp)₂Mo(OH)(H₂O)⁺. Intramolecular Attack of Hydroxide on Organic Substrates, Quality Control of 16332-06-2, the publication is Organometallics (2004), 23(8), 1738-1746, database is CAplus.

The hydrolysis of esters and difunctional ethers catalyzed by Cp’₂Mo(OH)(H₂O)⁺ (1) (Cp’ = η⁵-C₅H₄CH₃) and the stoichiometric oxidation of CO to CO₂ in the presence of 1 are described. These reactions, combined with the previously reported nitrile hydrations and phosphate esters hydrolyzes catalyzed by 1, demonstrate that 1 is an effective homogeneous catalyst for hydration, hydrolysis, and oxidation reactions in aqueous solution under mild conditions (pH ∼ 7, ∼ 80°). Each reaction is proposed to proceed by intramol. attack of the hydroxide ligand on a bound substrate. The intramol. nature of the reaction is supported by the ester hydrolysis activation parameters (ΔH^⧧ = 5.9 ± 0.7 kcal/mol and ΔS^⧧ = -48 ± 9 eu), the lack of H/D exchange, and the significant increase (10⁶-10⁸) in the rate of hydrolysis over uncatalyzed hydrolysis.

Organometallics published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Quality Control of 16332-06-2.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Breno, Kerry L. published the artcileOrganometallic Chemistry in Aqueous Solution. Hydration of Nitriles to Amides Catalyzed by a Water-Soluble Molybdocene, (MeCp)₂Mo(OH)(H₂O)⁺, Recommanded Product: 2-Methoxyacetamide, the publication is Organometallics (2003), 22(6), 1203-1211, database is CAplus.

[Cp’₂Mo(μ-OH)₂MoCp’₂]²⁺ (1) (Cp’ = η⁵-CH₃C₅H₄) is a precatalyst for the hydration of nitriles in aqueous solution under mild conditions (∼80°). Among the nitriles hydrated were acetonitrile, isobutyronitrile, benzonitrile, 3-hydroxypropionitrile, 3-bromopropioamide, 4-cyanopyridine, succinonitrile, Me cyanoacetate, 2-methoxyacetonitrile, and acrylonitrile. Except in the case of 2-methoxyacetonitrile, hydrolysis of the resulting amide products did not occur. Hydration of the C:C double bond did not occur in acrylonitrile, but hydrolysis of ester and ether linkages did occur in nitriles containing those functional groups. The apparent rate constants and turnover frequencies of the catalytic reactions were determined using an iterative kinetics-fitting program. The rates and turnover frequencies are comparable to those reported for many homogeneous nitrile hydration catalysts described in the literature. In aqueous solution, 1 is in equilibrium with [Cp’₂Mo(OH)(H₂O)]⁺ (2), and this monomer is proposed to be the active hydration catalyst. The hydration is proposed to occur by an intramol. attack of a hydroxide ligand on a coordinated nitrile. The hydration reaction is irreversibly inhibited by product and reversibly inhibited by substrate (nitrile).

Organometallics published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Recommanded Product: 2-Methoxyacetamide.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Lele, S. S. published the artcileCyanocoumarins, Name: 2-Methoxyacetamide, the publication is Journal of Organic Chemistry (1962), 637-9, database is CAplus.

Some cyanocoumarins were prepared by the Rosenmund-von Braun reaction on the halogenated coumarin in order to study their hydrolysis. The iodo derivative (0.01 mol) was mixed with 0.02 mol anhydrous CuCN, heated at the specified temperature 10 min., the mixture powd., extracted with either Me₂CO or AcOH, and the residue from the extract recrystallized from AcOH (needles). Addition of cyano derivative from a previous run to the mixture gave a higher yield. The following cyanocoumarins were thus obtained (coumarin, Rosenmund-von Braun reaction temperature, m.p., and % yield given): 7-methoxy-8-cyano, 180-90°, 269-70°, 60; 7-methoxy-3-cyano, 180-90°, 225-30°, 40; 7-methoxy-8-cyano-6-carbomethoxy, 210-20°, 102°, 54; 7-methoxy-8-cyano-4-carbomethoxymethyl, 190-210°, 192°, 22; 7-methoxy-8-cyano-4-Me, 220-30°, 289-91°, 55; 7-methoxy-3-cyano-4-Me, 180-5°, 223°, 75; 7-methoxy-8-cyano-4-methyl-6-carbomethoxy, 240-5°, 276°, 70; 7-methoxy-3-cyano-4-methyl-6-carbomethoxy, 250-5°, 249°, 70; 5-methoxy-8-cyano-4-Me, 260-70° 227-30° 46; 5-methoxy-8-cyano-4-methyl-6-carbomethoxy, 225-30° 236° 44. Hydrolysis A. The eyano compound (0.5 g.) was heated 2-3 h. with 90% H₂SO₄, the solid obtained on pouring the mixture on ice extracted with dilute NaHCO₃, and the product crystallized from AcOH. Method B. The cyanocoumarin (0.5 g.) was heated 2-3 h. with 10% alc. KOH, the product acidified, purified through NaHCO₃, and crystallized from AcOH. The following hydrolysis products from the cyanocoumarins mentioned above were obtained (hydrolysis method, product obtained, and m.p. given): A, 7-methoxy-8-carbamoyl, 277-9°; A, 7-methoxy-8-carbamoyl-6-carboxy, 267-8°; B, 7-methoxy8-cyano-6-carboxy, 228°; A, 7-methoxy-8-carbamoyl-4-acetic acid, 235-8°; B, 7-methoxy-8-cyano-4-acetic acid, 274-5° (and 7-methoxy-8-cyano-4-Me, -); A, 7-methoxy-8-carbamoyl-4-Me, 278°; A and B, 7-methoxy-4-methyl-3-carboxy, 184-5°; A, 7-methoxv-8-carbamoyl-4methyl-6-carboxy, 272°; B, 7-methoxy-8-cyano-4-methyl-6carboxy, 283°; A, 7-methoxy-4-methyl-3,6-dicarboxy, 20810°; B, 7-methoxy-3-cyano-4-methyl-6-carboxy, 248°; A, 5-methoxy-8-carbamoyl-4-Me, 286°; A, 5-methoxy-8carbamoyl-4-methyl-6-carboxy, 272°; B, 5-methoxy-8-cyano-4-methyl-6-carboxy, 248°. The carbamoyl derivative (0.5 g.) heated 3 h. at 120° with 18 mL. 50% H₂SO₄ and the mixture poured on ice gave the following results (method of hydrolysis, coumarin product obtained, m.p. given): III, 7-hydroxy-8-carboxy, 230°; 10% alkali or 50% H₂SO₄, 7-methoxy-6-carboxyl,-; 10% alkali or 50% H₂SO₄, 7-methoxy-4-Me, -; 10% alkali or 50% H₂SO₄, 7-methoxy-4methyl-8-carboxy, -; 10% alkali or 50% H₂SO₄, 7-methoxy-4-methyl-6-carboxy, -; 50% H₂SO₄, 5-methoxy-4-methyl-8-carboxy, 286°; 50% H₂SO₄, 5-methoxy-4-methyl-6,8-dicarboxy, 284°. The methoxycyanocoumarin was dissolved in Ac₂O, heated 3 h. with HI at 120°, and the product crystallized from AcOH. The following hydroxycyanocoumarins were thus obtained (coumarin and m.p. given): 7hydroxy-8-cyano, 305°; 7-hydroxy-8-cyano-4-Me, 272°; 7-hydroxy-3-cyano-4-Me, 298°; 5-hydroxy-8-cyano-4-Me, 276°.

Journal of Organic Chemistry published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Name: 2-Methoxyacetamide.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Okabe, Hiroyuki published the artcileAcceptor-Controlled Transfer Dehydration of Amides to Nitriles, Safety of 2-Methoxyacetamide, the publication is Organic Letters (2019), 21(12), 4767-4770, database is CAplus and MEDLINE.

Palladium-catalyzed dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions via the use of dichloroacetonitrile as a water acceptor. A key to the design of this transfer dehydration catalysis is the identification of an efficient water acceptor, dichloroacetonitrile, that preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst and makes the desired scheme exergonic, thereby driving the dehydration.

Organic Letters published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Safety of 2-Methoxyacetamide.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Marstokk, K.-M. published the artcileStructural and conformational properties of methoxyacetamide as studied by microwave spectroscopy and ab initio computations, Recommanded Product: 2-Methoxyacetamide, the publication is Acta Chemica Scandinavica (1996), 50(9), 845-847, database is CAplus.

Ab initio (6-311+G^** level) structure, rotational constants, dipole moments and energy differences of the three rotomers of methoxyacetamide found to be min. on the potential energy surface.

Acta Chemica Scandinavica published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Recommanded Product: 2-Methoxyacetamide.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Klages, Friedrich published the artcileOxonium salts. II. A new reaction for the preparation of trialkyloxonium salts, Application In Synthesis of 16332-06-2, the publication is Chemische Berichte (1953), 1322-6, database is CAplus.

cf. C.A. 47, 9897f. When 122 g. di-Me etherate (I) of HSbCl₆ in 100 cc. liquid SO₂ is treated at -30° with 32.5 g. N₂CHCO₂Et (II) while the mixture is stirred in a N stream, the SO₂ evaporated, and the residue triturated with ether, 97.5% trimethyloxonium hexachloroantimonate, [R₃O]⊕SbCl₆ symmetric difference symbol (III) (R = Me), sandlike crystals, m. 159°, is obtained. III are formed according to the reactions: R₂O.HSbCl₆ + II → [EtO₂CCH₂O⊕R₂]SbCI₆ symmetric difference symbol (IV) + N₂; IV + R₂O → EtO₂CCH₂OR + III. Evaporating the ether solution gives 50% MeOCH₂CO₂Et, b₁₃ 41-5°, b. 131° (amide, m. 92°). The di-Et homolog (48 g.) of I, treated in 100 cc. CH₂Cl₂ with 11.4 g. II at 10° and the residue triturated with ether gives 85% III (R = Et), m. 133°, and 2% EtOCH₂CO₂Et, b₁₃ 53° (amide, m. 82°). Adding dropwise 29.9 g. SbCl₅ to 20.4 g. Pr₂O in 100 cc. SO₂ at -70° and treating the precipitate with HCl give 100% Pr homolog of I, m. 72° (sealed tube, decomposition), which, treated in CH₂Cl₂ with II gives 73% III (R = Pr), m. 105° (decomposition). Adding 29.9 g. SbCl₅ dropwise to 26 g. Bu₂O in 100 cc. SO₂ while simultaneously passing HCl and N through the mixture and evaporating the SO₂ give 60 g. Bu homolog of I, m. 45-54° (sealed tube, decomposition), which with II in CH₂Cl₂ yields 33% III (R=Bu), m. 119° (decomposition). Saturating 60 g. SbCl₅ in 50 cc. CH₂Cl₂ at -70° with dry HCl in a Natm. and then adding very slowly 41 g. (Me₂CH)₂O (the mixture must not turn red) give 87% Me₂CH homolog (V) of I, m. 104°(decomposition). Adding 15.2 g. II dropwise to 72 g. V in 200 cc. CH₂Cl₂ at -5° and treating the precipitate repeatedly in CH₂Cl₂with II gives 9% [EtO₂CCH₂O(CHMe₂)₂]⊕SbCl₆ symmetric difference symbol, m. 116° (decomposition); di-iso-Am homolog, 5%, m. 89° (decomposition).

Chemische Berichte published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Application In Synthesis of 16332-06-2.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Kumaresan, R. published the artcileSynthesis and evaluation of N,N-di-alkyl-2-methoxyacetamides for the separation of U(VI) and Pu(IV) from nitric acid medium, Category: ethers-buliding-blocks, the main research area is preparation methoxyacetamide extractant uranium plutonium fuel reporcessing.

The homologs of N,N-di-alkyl-2-methoxyacetamides (DAMeOA) having three different alkyl chains varying from hexyl to decyl (C6, C8 and C10) were synthesized and characterized by NMR and IR spectral analyses. Extraction behavior of U(VI) and Pu(IV) from nitric acid medium in a solution of 0.5 M of DAMeOA in n-dodecane (n-DD) was studied and the results were compared with those obtained using N,N-di-hexyloctanamide (DHOA) in n-dodecane. The effect of various parameters on the distribution ratio of U(VI) and Pu(IV) in DAMeOA was studied. The extraction of nitric acid increased with decrease in chain length of alkyl group attached to amidic nitrogen atom of DAMeOA and the conditional nitric acid extraction constant was determined The extraction of nitric acid in DAMeOA/n-DD resulted in the formation of third phase in organic phase and the third phase occurred early with DAMeOA having smaller alkyl chain length. In contrast to this, the distribution ratio (D) of U(VI) and Pu(IV) in DAMeOA/n-DD increased with increase in the concentration of nitric acid and with increase in the chain length of alkyl group attached to amidic nitrogen atom of DAMeOA. The stoichiometry of the metal – solvate was determined from the slope of extraction data. Quant. recovery of uranium and plutonium from the loaded organic phase was achieved using dilute nitric acid.

Radiochimica Acta published new progress about Extractants. 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Category: ethers-buliding-blocks.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem