Justin M. Lopchuk, in Progress in Heterocyclic Chemistry, 2017. Shareable Link. Please check your email for instructions on resetting your password. and HTML 5 enabled browser. The 3,2-benzothiazepine 3,3-dioxide (385) has been prepared in high yield from (384) by intramolecular sulfonyl-amidomethylation 〈76CC470〉. DESCRIPTION; APPLICATION; INDUSTRIES USED; VARSAL ADVANTAGE; Other names: ethanimidamide, ethanamidine acetimidamide, carboxamidine, carboximidamide; Molecular weight: 94.54; Appearance: white or yellowish long prismatic crystals; CAS#: 124-42-5; Used as a Vitamin B1 building block, strong non-ionic nucleophile, intermediate in antihypertensive APIs, … Molecular Weight: 94.54. (M-F, 8AM-7PM EST) The mixture was then poured into 50 ml water and extracted twice with 50 ml EtOAc. The product was purified by chromatography (EtOAc/hexanes, 1:4). Institute of Standards and Technology, nor is it intended to imply This method of obtaining AA GC adopted us for the prototype. The results suggest that other N-heterocycles containing fluorine substituents can also complete the reaction via these reaction conditions and yield the target products. and you may need to create a new Wiley Online Library account. (M-F, 8AM-5PM EST) Tel: 1-800-343-0660 or 1-978-521-6300 A solution of 3,5-dimethyl-3H-imidazole-4-carboxylic acid (7.14 mmol) and 1,1ʹ-carbonyl-diimidazole (10.7 mmol) in 35 ml DMF was stirred 3 hours at ambient temperature and then treated with N-hydroxy-acetamidine (9.18 mmol). 2-Aminoalkylarsines (29) react with iminoester hydrochlorides (30) to give the corresponding 1,3-azaarsolines (31) with the desired imidoylarsenic grouping (Equation (9)) <76JPR409, 89ZC71>. Tel: 1-888-343-8025 or 1-978-521-6401 The reactions proceeded smoothly to furnish the respective substituted 1,3,5-triazines in good to excellent isolated yields. Compound (381), prepared by direct chlorosulfonation, was converted to (382) and thence to the 1,2-benzothiazepin-3-one system (383) 〈76JHC1309〉. For the best experience on our site, be sure to turn on Javascript in your browser. Please check your email for instructions on resetting your password. N,N′-Bis(trimethylsilyl)benzamidine forms a 2:1 complex 136 with aluminum trichloride in high yield as shown in Equation (65). carefully selected solvents, and hence may differ in detail By continuing you agree to the use of cookies. For example, phenylethylarsine was treated with one equivalent of n-butyllithium (in hexane/diethylether), followed by N-phenylbenzimidoyl chloride at 0 °C to give a 73% yield of the imidoylarsenic derivative (34) as shown in Equation (10). The aqueous phase was washed twice with 20 ml EtOAc, filtered, then concentrated, and an oily yellow solid isolated. © 2018 by the U.S. Secretary of Commerce email: [email protected], Specialty/Bulk Sales The solution was concentrated and the residue poured into 40 ml saturated NaHCO3 solution, then extracted twice with 30 ml CH2Cl2. Remove contact lenses, if present and easy to do. : AC170210000; AC170210100; AC170211000; AC170215000 CAS-No 124-42-5 Synonyms Ethanimidamide hydrochloride. Though alkyl halides are often poor substrates in such coupling reactions, Martin has reported conditions for addition to aldehydes, where the resulting product carbinols are deoxygenated using a Barton-type protocol <92TL1839>. Clear. This item can also be found in the following categories: It is hygroscopic. By browsing our website without changing the browser settings you grant us permission to store that information on your device. One general method of preparing aluminum or gallium complexes is shown in Scheme 39. acetamidine hydrochloride. The product reacted with acetyl chloride and then with alcohols to give the 1-alkoxy-2-acyl derivatives, and was oxidized to the 3,3-dioxide. Treatment of carbodiimides with trimethylaluminum gives the dimethylaluminum acetamidine complex 131 (alkyl = iPr, tBu, cyclohexyl). Search by Name, CAS, MDL, Catalogue, SMILES, IUPAC, Skip to the beginning of the images gallery, This product is considered non-hazardous for transport. Title: Acetamidine Hydrochloride. The process is versatile, tolerant of latent functionality, and complements existing methods for the introduction of this important moiety <81JFC(18)197, 82TL2323, 89JOC613, 89TL7013, 91TL1019>. PNAS. Learn more. Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. Fax: 1-800-322-4757 acetamidine sulfate (1:1) acetamidinium All Rights Reserved. Fax: 1-978-521-6350 errors or omissions in the Database. Use the link below to share a full-text version of this article with your friends and colleagues. We use cookies to help provide and enhance our service and tailor content and ads. The nickel approach also facilitated dimerization of a dialkyl (iodotetrafluoroethyl)phosphonate, giving the coupled product in 48% yield <94JOC2393>. And 1,3,5-triazines were obtained in good yields. Remove contact lenses, if present and easy to do. Nitinol™ Nickel Titanium Shape Memory Alloys, Specpure® Inorganic Standards for Water Analysis, Specpure® Oil-Based Standards for Wear Metal Analysis, Specpure® XRF Standards for Petroleum Products, Cellular Growth & Attachment Factors - BT Products, POCO Electron Beam Crucibles & Hearth Shields (Carbon Graphite), Boron, Phosphorus, Silicon, and Sulfur Compounds, Sugars, Steroids, Amino Acids, and Nucleotides, Precious Metal Compounds - Homogeneous Catalysts. Preparation of 5-(2-bromo-3,5-dimethyl-3H-imidazol-4-yl)-3-methyl-[1,2,4]-oxadiazole. Then benzaldehyde with electron-donating or electron-withdrawing groups were chosen as the substrates. Use the link below to share a full-text version of this article with your friends and colleagues. The interactive spectrum display requires a browser with JavaScript and This mixture was stirred 2 hours at 100°C and was then reconcentrated. The 4,5-dihydro-3,2-benzothiazepine (380) has been prepared by the thermally induced ring expansion of 1-azidoisothiochroman 〈74LA734〉. The corresponding dialkyl (bromodifluoromethyl)phosphonates fail to undergo this coupling using cadmium, but this was finally effected using a nickel derivative. Uses advised against Food, drug, pesticide or biocidal product use. If the reactions are prolonged, a second substitution occurs giving a monohalobis(dialkylphosphinyl) derivative. that these items are necessarily the best available for the purpose. acetamidine monoacetate. First, they used indole-2-carbaldehyde and, Synthesis: Carbon With Two Attached Heteroatoms With at Least One Carbon-to-Heteroatom Multiple Link, Comprehensive Organic Functional Group Transformations II, . Select a region with data to zoom. Reaction of o-arsinophenols (42) with imidoyl chlorides (for example (43), N-phenylbenzimidoyl chloride) proceeds via a primary attack of the arsino group to give the hydrochloride salt of an imidoylarsine (44) <80JOM(186)39>. acetamidine sulfate (1:1) acetamidinium Additional Names: ethanamidine hydrochloride; a-amino-a-iminoethane hydrochloride; ethenylamidine hydrochloride; acediamine hydrochloride. The pyrimidine synthesis from benzofurans is very specialized, leading only to 5-(o-hydroxyphenyl)pyrimidines. been selected on the basis of sound scientific judgment. 1H NMR (CDCl3) δ 4.16 (2H, s, CH2), 7.21–7.48 (8H, m, ArH), 8.02 (1H, m, ArH), 8.28 (1H, m, ArH), 8.70 (1H, bs, NH), Preparation of 3-(3-Benzyl-[1,2,4]-oxadiazol-5-yl)-1-[2-(pyrrolidin-1-yl)ethyl]-1H-indole. Working off-campus? Clear, Add the items to your existing shopping cart? Tel: 1-800-343-7276 or 1-978-521-6405 In 2012, Batra developed a one-step synthesis of 1,3,5-triazines through a copper-catalyzed cascade reaction, which gave products in moderate to good yields (Scheme 5.5) [5]. 1996, 93, (24),13617-13622, Hazard Statements: JavaScript seems to be disabled in your browser.