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

HRID 376986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 376986
[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 reactions about 2/3 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. distillationAfter the reactions about 2/3 by volume of ethanol was distilled off under reduced pressure
  4. additionEther was added little by little to the reaction mixture
  5. customto precipitate crystals
  6. filtrationThe crystals were collected by filtration
  7. washwashed with a mixture of ethanol and ether

Quellen und Nachweise

ORD-Eintrag
ord-88a7c9d3df984d6f85dfac98ebe72700
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06022967

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