3-methylsulfanylpropanenitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-sulfamyl-acrylamidine was prepared by a four-step procedure from 3-(methylthio)-propionitrile, with an extremely low (5.5%) yield in several days. The products of the subsequent steps, including famotidine, were isolated by column chromatography. yield in several days were isolated by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the U.S. Pat. No. 4,496,737 (Merck) 3-(methylthio)-propionitrile was used as a starting material, which was converted into the corresponding imino-ether base with a yield of 67.2%. The oily product obtained was boiled with 1.5 molar equivalents of sulfamide, for 20 hours. After recovering the excess of sulfamide the product was isolated by column chromatography, with a moderate (26.0%) yield. The N-sulfamyl-3-(methylthio)-propionamide obtained was oxidized into the corresponding sulfoxide with m-chloroperbenzoic acid in a mixture of chloroform and methanol (yield: 83.4%). The sulfoxide compound was then subjected to an elimination reaction by boiling with triethyl amine in an ethanolic medium for 20 to 30 hours. As a result, N-sulfamyl-acrylic amidine of the formula (IV) ##STR6## was isolated by column chromatography with a yield of 37.2%. The oily product obtained After recovering the excess of sulfamide the product was isolated by column chromatography, with a moderate (26.0%) yield