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ChemicalBook CAS DataBase List Ranitidine

Ranitidine synthesis

1synthesis methods
Ranitidine, N[2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]- N′-methyl-2-nitro-1,1-ethendiamine (16.2.8), is synthesized from furfuryl alcohol, which undergoes aminomethylation reaction using dimethylamine and paraform, which form 5- (dimethylaminomethyl)furfuryl alcohol (16.2.6). Further reaction with 2-mercaptoethylamine hydrochloride gives a product of substitution of the hydroxyl group in (16.2.6), 5-dimethylaminomethyl-2-(2′-aminoethyl)thiomethylfurane (16.2.7). Reacting this with Nmethyl- 1-methylthio-2-nitroethenaamine gives ranitidine (16.2.8).

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Yield:66357-35-5 92%

Reaction Conditions:

in water at 55;

References:

Galkin, Konstantin I.;Krivodaeva, Elena A.;Romashov, Leonid V.;Zalesskiy, Sergey S.;Kachala, Vadim V.;Burykina, Julia V.;Ananikov, Valentine P. [Angewandte Chemie - International Edition,2016,vol. 55,# 29,p. 8338 - 8342][Angew. Chem.,2016,vol. 128,# 29,p. 8478 - 8482,5] Location in patent:supporting information

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