N-Methyl methanesulfonamide, 500 grams.
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MSDS: Safety Data Sheet
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Q1: What is the molecular formula and weight of N-Methylmethanesulfonamide?
A: N-Methylmethanesulfonamide has the molecular formula C2H7NO2S and a molecular weight of 125.17 g/mol. []
Q2: What is the conformational preference of N-Methylmethanesulfonamide in the solid state?
A: X-ray crystallography at low temperature revealed that N-Methylmethanesulfonamide adopts a gauche conformation in the solid state, with both the methyl group and the amide hydrogen atom in a gauche orientation relative to the sulfonyl methyl group. [, ]
Q3: Can you describe the dissolution behavior of N-Methylmethanesulfonamide?
A: While specific dissolution rate data is not provided in the papers, N-Methylmethanesulfonamide is known to be a polar liquid at room temperature, suggesting good solubility in polar solvents like water. [, ]
Q4: How does the introduction of a pyrazoline ring at the C5 position of Rosuvastatin, using N-[4-(4-fluorophenyl)-5formyl-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide as a starting material, impact antimicrobial and anti-inflammatory activity?
A: Research suggests that incorporating a pyrazoline ring at the C5 position of Rosuvastatin, derived from N-[4-(4-fluorophenyl)-5formyl-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide, can lead to compounds with significant antimicrobial and anti-inflammatory activities. Notably, compounds with specific substituents on the pyrazoline ring displayed potent inhibition against various pathogenic organisms and exhibited promising anti-inflammatory effects in a carrageenan-induced rat paw oedema model. []
Q5: How does modifying the N-Methylmethanesulfonamide moiety in Sumatriptan derivatives impact their vasoconstriction properties?
A: Studies on Sumatriptan, a drug used for migraine treatment, and its derivatives indicate that modifications to the N-Methylmethanesulfonamide moiety can significantly alter their vasoconstriction activity. Specifically, replacing the sulfonamide group with an amidine function, while maintaining the 3-aminoethyl indole core structure, resulted in compounds that induced rapid and sustained vasoconstriction in the carotid arterial circulation, suggesting potential for migraine therapy. []
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Q6: What are some synthetic applications of N-Methylmethanesulfonamide?
A: N-Methylmethanesulfonamide serves as a versatile building block in organic synthesis. For instance, it reacts with 2-chloronicotinonitrile under basic conditions to afford the pyrido[2,3-c]-1,2-thiazine ring system. [] Additionally, it plays a crucial role in constructing the benzofuro[2,3-c][1,2]thiazine ring system when reacted with 2-chloro-3-benzofurancarboxaldehyde, which is obtained by treating 2-coumaranone with the Vilsmeier reagent. []
Q7: Can N-Methylmethanesulfonamide be used to synthesize sulfonylisocyanates?
A: Yes, N-Methylmethanesulfonamide reacts with chlorosulfonylisocyanate to form an intermediate, which upon heating, undergoes rearrangement to yield sulfonylisocyanates. These compounds are valuable intermediates in the synthesis of herbicides. []
Q8: How is N-Methylmethanesulfonamide employed in the synthesis of Rosuvastatin?
A: N-Methylmethanesulfonamide is a crucial building block in the multi-step synthesis of Rosuvastatin, a HMG-CoA reductase inhibitor used to lower cholesterol levels. One approach utilizes N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (2) as a key intermediate. This aldehyde (2) is synthesized via a palladium-catalyzed formylation reaction and subsequently coupled with a specific ylide in a Wittig reaction to construct the Rosuvastatin precursor. [] Further transformations, including stereoselective reduction, ultimately lead to Rosuvastatin. []
Q9: Have there been any ab initio calculations performed on N-Methylmethanesulfonamide?
A: Yes, ab initio calculations have been conducted on N-Methylmethanesulfonamide to investigate its conformational preferences and to develop force field parameters for molecular mechanics simulations. These calculations provide insights into the molecule's rotational barriers and electronic structure. [, ]
Q10: Is there evidence suggesting the involvement of N-Methylmethanesulfonamide-containing compounds in modulating ion channel activity?
A: Research indicates that compounds containing the N-Methylmethanesulfonamide moiety can exhibit potent and selective ion channel modulation. For instance, HMR [(3R,4S)-(+)-N-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy) chroman-4-yl]-N-methylmethanesulfonamide] acts as a highly selective blocker of the slowly activating delayed rectifier potassium current (IKs) in canine left ventricular myocytes. This compound demonstrates greater potency and specificity compared to other known IKs blockers. [] Furthermore, mefenamic acid, although lacking the N-Methylmethanesulfonamide moiety itself, requires the presence of the KCNE1 subunit for its IKs activation activity. []
Q11: How is the degradation of amidosulfuron, a herbicide containing the N-Methylmethanesulfonamide moiety, studied, and what are the identified degradation products?
A: The photodegradation of amidosulfuron in aqueous solutions under simulated sunlight has been investigated using a combination of analytical techniques, including ultrahigh-pressure liquid chromatography with a UV detector (UHPLC-UV), ultrahigh-pressure liquid chromatography-mass spectrometry (UHPLC-MS), and Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS). [] The degradation pathway involves the loss of various fragments, including methylsulfamic acid (CH5NO3S), sulfocarbamic acid (CH3NO5S), carbamic acid (CH3NO2), methyl(methylsulfonyl)sulfamic acid (C2H7NO5S2), N-methylmethanesulfonamide (C2H7NO2S), and sulfonic acid (H2SO4), indicating O- and S-demethylation and hydroxylation processes. []
Q12: What analytical techniques are employed to characterize the intermediate N-[4-(4-Fluorophenyl)-5-(hydroxymethyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide in Rosuvastatin synthesis?
A: The Rosuvastatin intermediate, N-[4-(4-Fluorophenyl)-5-(hydroxymethyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide, is characterized using Nuclear Magnetic Resonance (NMR) spectroscopy and Liquid Chromatography-Mass Spectrometry (LC-MS). Additionally, its crystal structure is determined by X-ray diffraction, revealing its crystallization in the monoclinic system, space group C2/C. []