ChemInform Abstract: Synthesis of Ranitidine

Глушков, Р. Г.; Adamskaya, E. V.; Vozyakova, T. I.; Oleinik, A. F.

doi:10.1002/chin.199104351

Cited by 2 publications

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“…5,6 1-Methylamino-l-methylthio-2-nitroethene is a crucial intermediate for the manufacture of ranitidine. 7 The synthesis of nitroketene N,S-acetals (3) are usually performed by reaction of l,l-bis(methylthio)-2-nitroethene (1) with one equivalent of several primary or secondary amines (Scheme 1). 1,8,9 A second approach to the synthesis of nitroketene N,S-acetals is performed by adding nitromethane anion to methyl isocyanate, followed by S-methylation.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of Nitroketene N,S-Arylaminoacetals

Sangi¹,

Corrêa²

2010

J. Braz. Chem. Soc.

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Neste trabalho nós relatamos o uso de microondas como fonte de energia para promover a síntese de uma série de nitroeteno N,S-acetais com bons rendimentos. Estes compostos são intermediários muito úteis para a síntese de sistemas heterocíclicos nitrogenados.In this paper we report the use of microwaves as heat source to promote the synthesis of a series of nitroketene N,S-acetals with good to excellent isolated yields. These compounds are very useful intermediates for synthesizing nitrogen-containing heterocycles.

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Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of Nitroketene N,S-Arylaminoacetals

Sangi¹,

Corrêa²

2010

J. Braz. Chem. Soc.

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“…3 A key intermediate in the synthesis of 1 is 1-methylthio-1-methylamino-2-nitroethylene 7. This can be prepared by addition of the nitromethane anion to CS 2 and methylation to give 1,1-bis(methylthio)-2-nitroethylene 6, followed by substitution of one of the MeS groups with methylamine (Scheme 2).…”

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confidence: 99%

“…Other approaches to 1 have been developed which avoid the use of cysteamine altogether, in which the OH group of either 3 or 4 is converted to SH and then aminoethylated using aziridine, 2-chloroethylamine, chloroacetonitrile, or N-(2chloroethyl) phthalimide. 3 A key intermediate in the synthesis of 1 is 1-methylthio-1-methylamino-2-nitroethylene 7. This can be prepared by addition of the nitromethane anion to CS 2 and methylation to give 1,1-bis(methylthio)-2-nitroethylene 6, followed by substitution of one of the MeS groups with methylamine (Scheme 2).…”

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confidence: 99%

“…Yet another alternative is the reaction of 5 with either methyl isocyanate or methyl isothiocyanate and subsequent replacement of the chalcogen by nitromethane. 3,12 Finally, the right hand side of the molecule can be built up first and linked to 4 or a derivative thereof in which the OH has been converted into a leaving group (halide, sulfonate ester) as shown in Scheme 3. We have recently shown that 5-(chloromethyl)furfural (CMF) 12 can be derived in a single step from either sugars, cellulose, or raw cellulosic biomass in isolated yields between 80-90%, 13 and are now in the course of developing new applications and markets for this renewable platform chemical.…”

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Synthesis of ranitidine (Zantac) from cellulose-derived 5-(chloromethyl)furfural

Mascal

Dutta

2011

Green Chem.

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The biomass-derived platform chemical 5-(chloromethyl)furfural is converted into the blockbuster antiulcer drug ranitidine (Zantac) in four steps with an overall 68% isolated yield.Ranitidine 1, sold under the trade name Zantac, is a histamine H 2 -receptor antagonist which is used in the management of gastroesophageal reflux disease (GERD) and the treatment of gastric and duodenal ulcers. It was introduced by Glaxo (now GlaxoSmithKline) in 1981 and by 1986 had total sales in excess of $1 billion, the first-ever drug to achieve this milestone. 1 Although Zantac has been largely surplanted as a prescription drug by modern proton pump inhibitors such as omeprazole (Prilosec) and esomeprazole (Nexium), it has recently been reformulated for over-the-counter sales as a general antacid preparation.The synthesis of ranitidine 1 has been described for the most part in the patent literature, and has been the subject of multiple reviews. 2-5 Given the commercial interest in this molecule, all of the synthetically reasonable disconnections have been probed in one way or another, but perhaps the most straightforward approach up to now remains that which was described in the original patent (Scheme 1). 6 This route starts from furfuryl alcohol 3, which can be sourced from the reduction Scheme 1 Reagents a. H 2 , cat.; b. CH 2 O, Me 2 NH, H + cat.; c. HSCH 2 CH 2 NH 2 , aq. HCl; d. 7.

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ChemInform Abstract: Synthesis of Ranitidine

Cited by 2 publications

References 0 publications

Microwave-assisted synthesis of Nitroketene N,S-Arylaminoacetals

Microwave-assisted synthesis of Nitroketene N,S-Arylaminoacetals

Synthesis of ranitidine (Zantac) from cellulose-derived 5-(chloromethyl)furfural

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