- Cyanide-Free One-Pot Synthesis of Methacrylic Esters from Acetone
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Methacrylic esters, represented by methyl methacrylate (MMA), are widely used as commodity chemicals. Here, the one-pot synthesis of methacrylic esters from acetone, a haloform and alcohols in the presence of an organic base is described. Using DBU as the organic base for the reaction of acetone, chloroform and methanol in acetonitrile afforded MMA in 66 % yield. When the solvent was replaced by benzonitrile, the product MMA was successfully purified by distillation. Applicability of this process to various alcohols was also investigated to show ethyl, phenyl, CF3CH2, and n-C6F13CH2CH2 esters were obtained in moderate yields. The use of bromoform instead of chloroform resulted in the improvement of the yield, for example, methyl and n-C6F13CH2CH2 esters up to 81 and 70 %, respectively. The reaction with deuterated starting materials acetone-d6 and MeOH-d4, with DBU in acetonitrile afforded deuterated MMA (MMA-d8) in 70 % yield.
- Koyama, Minoru,Kawakami, Takafumi,Okazoe, Takashi,Nozaki, Kyoko
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supporting information
p. 10913 - 10917
(2019/08/02)
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- N-Acyl-N'-(pyridin-2-yl) Ureas and Analogs Exhibiting Anti-Cancer and Anti-Proliferative Activities
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Described are compounds of Formula 1 which find utility in the treatment of cancer, autoimmune diseases and metabolic bone disorders through inhibition of c-FMS (CSF-1R), c-KIT, and/or PDGFR kinases. These compounds also find utility in the treatment of other mammalian diseases mediated by c-FMS, c-KIT, or PDGFR kinases.
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Paragraph 0244
(2014/09/29)
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- N-Acyl-N'-(pyridin-2-yl) Ureas and Analogs Exhibiting Anti-Cancer and Anti-Proliferative Activities
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Described are compounds of Formula I which find utility in the treatment of cancer, autoimmune diseases and metabolic bone disorders through inhibition of c-FMS (CSF-1R), c-KIT, and/or PDGFR kinases. These compounds also find utility in the treatment of other mammalian diseases mediated by c-FMS, c-KIT, or PDGFR kinases.
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Paragraph 0375
(2014/09/30)
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- Hypervalent iodine oxidation of trimethylsilyl ketene acetals: A convenient route to α-methoxylation of esters and lactones
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Hypervalent iodine oxidation of trimethylsilyl ketene acetals of esters and lactones using iodosobenzene in methanol affords the corresponding α- methoxylated carbonyl compounds in good yields.
- Moriarty, Robert M.,Rani, Neena,Condeiu, Cristian,Duncan, Michael P.,Prakash, Om
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p. 3273 - 3277
(2007/10/03)
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- Piperidine derivatives, compositions and use
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Compounds of formula I, Ia or Ib and pharmaceutically acceptable salts thereof, useful in the treatment of neuropsychiatric disorders such as psychoses; pharmaceutical compositions comprising a compound of formula I and a pharmaceutically acceptable diluent or carrier; and methods of treating neuropschiatric disorders comprising administering to a mammal (including man) in need of such treatment an effective amount of a compound of formula I, or a pharmaceutically acceptable salt thereof; STR1
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- Process for producing methyl methacrylate
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Disclosed is a process for producing methyl methacrylate which comprises: (I) a step of reacting prussic acid and acetone to form acetonecyanhydrin; (II) a step of hydrating the acetonecyanhydrin obtained in the step (I) to form α-hydroxyisobutyric acid amide; (III) a step of dehydrating the α-hydroxyisobutyric acid amide obtained in the step (II) to form methacrylic acid amide; (IV) a step of reacting the methacrylic acid amide obtained in the step (III) and methyl formate to form methyl methacrylate and formamide; and (V) a step of dehydrating formamide separated from the product obtained in the step (IV) to form prussic acid and recycling said prussic acid as a starting material in the step (I). The process produces methyl methacrylate with high selectivity without undesirable by-product such as ammonium sulfate.
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- Ether isonitriles and radiolabeled complexes thereof
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Ether-substituted isonitriles, Tc99m complexes thereof, and processes for myocardial tissue radioimaging using the Tc99m complexes.
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- Mass Spectrometry of 2-Alkylthio-2-methylpropanoic Acids and Their Esters and Amides. Structural and Steric Effects on the McLafferty Rearrangement
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The electron ionization mass spectra (MS) of S-methylated derivatives of N-(2-mercapto-2-methylpropanoyl)-L-cysteine and 2-alkylthio-2-methylpropanoic acids, as well as their esters and amides, were examined.Use of the deuterium labeling technique and accurate mass measurement supported the proposed fragmentation pathways.Extensive loss of CH2S from a molecular ion by the McLafferty rearrangementof a primary hydrogen is important in the MS of S-methyl compounds of amide derivatives.It was demonstrated that the intensity of the rearrangement ion decreases in the order of amide, ester, and acid, and in the case if amides the reaarangement is suppressed by the nonbonded interaction between methyl groups on the α carbon and the amide nitrogen.Keywords-N-(2-mercapto-2-methylpropanoyl)-L-cysteine; 2-alkylthio-2-methylpropanoic acid and methyl ester; 2-alkylthio-2-methylpropanamide; electron impact mass spectrometry; McLafferty rearrangement; steric interaction
- Mori, Yuji,Fujiwara, Shigeru,Miyachi, Toshiko,Kitanishi, Hiroyuki,Oya, Masayuki,et al.
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p. 1505 - 1517
(2007/10/02)
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- ELECTROCHEMICAL OXIDATION OF ALKYL-SUBSTITUTED ALLENES IN METHANOL
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Mono-, di- and tri-alkyl-substituted allenes were potentiostatically oxidized in methanol at graphite and Pt anodes.At the former electrode, α-methoxylated ketones (due to 4F/mole electricity consumption) and esters (6F/mole) were the major products.At a Pt anode, intermediate products such as vinyl-ether derivatives (2F/mole) were characterised too.Unlike the anodic oxidation of alkenes and alkynes previously reported in the literature, dimerisation is not a typical process in the allenes' oxidation, since of all the products obtained only a sole dimer has been observed.The mechanism for the formation of most products is discussed.
- Becker, James Y.,Zinger, Baruch
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p. 1677 - 1682
(2007/10/02)
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