Nitroxyl → N-sulfamyl-3-(methylthio)-propionamide
Reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5]#[N:6].N=[O:8].[S:9]([NH2:13])(N)(=[O:11])=[O:10]>>[S:9]([NH:6][C:5](=[O:8])[CH2:4][CH2:3][S:2][CH3:1])(=[O:11])(=[O:10])[NH2:13]Participants
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%.
Workup
- customThe oily product obtained
- customAfter recovering the excess of sulfamide the product
- customwas isolated by column chromatography, with a moderate (26.0%)
- customyield
Sources & evidence
- ORD record
- ord-89884e8813e741a5ba583567ea852ae1
- Source dataset
- uspto-grants-1989_05
- Patent number
- US04835281
Reaction notes
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