Chlorosuccinimide → 1-(3-chlorotetrahydro-2H-1,3-thiazin-2-ylidene)-3-(2,4-dichlorophenoxy)-1-nitro-2-propanone

HRID 2398043

Reaktionsgleichung

Reaktionsgleichung von HRID 2398043
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6](=[O:17])[C:7]([N+:14]([O-:16])=[O:15])=[C:8]1[NH:13][CH2:12][CH2:11][CH2:10][S:9]1.[Cl:23]N1C(=O)CCC1=O.[O-][Si]([O-])=O.[Mg+2]>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Cl:23][N:13]1[CH2:12][CH2:11][CH2:10][S:9][C:8]1=[C:7]([N+:14]([O-:16])=[O:15])[C:6](=[O:17])[CH2:5][O:4][C:3]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:2]=1[Cl:1]

Komponenten

6

Edukt 3

HCID 31398ChlorosuccinimideHCID 61680MAGNESIUM SILICATE (synthetic)HCID 867346973-(2,4-dichlorophenoxy)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-propanone

Produkt 1

HCID 536853201-(3-chlorotetrahydro-2H-1,3-thiazin-2-ylidene)-3-(2,4-dichlorophenoxy)-1-nitro-2-propanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3.6 g of 1 and 2.1 g of N-chlorosuccinimide were combined in 150 ml of carbon tetrachloride and the mixture was refluxed for 1 hour. The resulting mixture was filtered through Celite and the solvent was evaporated to give a liquid, which was triturated in ether, decolorized with activated charcoal and filtered through Celite and stripped of solvent to give a yellow cloudy liquid. This was passed through Florisil, using methylene chloride as eluent; then stripped to give an oil, which was kept in a refrigerator over a week-end. Part of the oil crystallized. On scratching, more crystals formed. Separation of the crystals gave 2, as bright yellow crystals, m.p. 103°-105°.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 hour
  2. filtrationThe resulting mixture was filtered through Celite
  3. customthe solvent was evaporated
  4. customto give a liquid, which
  5. customwas triturated in ether
  6. filtrationfiltered through Celite
  7. customto give a yellow cloudy liquid
  8. customto give an oil, which
  9. waitwas kept in a refrigerator over a week
  10. customPart of the oil crystallized
  11. custommore crystals formed
  12. customSeparation of the crystals
  13. customgave 2

Quellen und Nachweise

ORD-Eintrag
ord-ef2eb43ad0c849a29ce457c530052334
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04024138

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