1,1-Bis(methylthio)-2-nitroethylene → 3-(3-pyridylmethyl)2-nitromethylenetetrahydro-2H-1,3-thiazine

HRID 379285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379285
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][SH:12])[CH:2]=1.[N+:13]([CH:16]=[C:17](SC)SC)([O-:15])=[O:14]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][S:12][C:17]2=[CH:16][N+:13]([O-:15])=[O:14])[CH:2]=1

Komponenten

4

Edukt 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 13752794N-(3-pyridylmethyl)3-aminopropanethiol

Produkt 1

HCID 539788653-(3-pyridylmethyl)2-nitromethylenetetrahydro-2H-1,3-thiazineAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of N-(3-pyridylmethyl)3-aminopropanethiol (1.8 g), 1-nitro-2,2-bis(methylthio)ethylene (1.7 g) and ethanol (40 ml) was heated under reflux for 5 hours under a nitrogen stream. After the reaction, about ⅔ by volume of ethanol was distilled off under reduced pressure. Ether was added little by little to the reaction mixture to precipitate crystals. The crystals were collected by filtration, and washed with a mixture of ethanol and ether to give the desired 3-(3-pyridylmethyl)2-nitromethylenetetrahydro-2H-1,3-thiazine (1.2 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours under a nitrogen stream
  3. customAfter the reaction
  4. distillationabout ⅔ by volume of ethanol was distilled off under reduced pressure
  5. additionEther was added little by little to the reaction mixture
  6. customto precipitate crystals
  7. filtrationThe crystals were collected by filtration
  8. washwashed with a mixture of ethanol and ether

Quellen und Nachweise

ORD-Eintrag
ord-778f42141cf1414b9606b7cf4651e013
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297374B1

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