Nitroxyl → N-sulfamyl-3-(methylthio)-propionamide

HRID 1762975

반응식

HRID 1762975 반응식
[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]

참가 물질

4

반응물 3

HCID 945NitroxylHCID 82267SulfamideHCID 5483863-(Methylsulfanyl)propanenitrile

생성물 1

HCID 20040173N-sulfamyl-3-(methylthio)-propionamide수율 67.2%

실험 절차

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%.

후처리

  1. customThe oily product obtained
  2. customAfter recovering the excess of sulfamide the product
  3. customwas isolated by column chromatography, with a moderate (26.0%)
  4. customyield

출처 및 근거

ORD 기록
ord-89884e8813e741a5ba583567ea852ae1
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04835281

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