Methyl thiocyanate → HCID 22489889, Verbindung

HRID 2179940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179940
B(Cl)(Cl)Cl.[F:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].CS[C:16]#[N:17].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[F:5][C:6]1[C:7]([CH3:13])=[CH:8][C:9]([OH:12])=[C:10]([CH:11]=1)[C:16]#[N:17]

Komponenten

6

Edukt 4

HCID 11168Methyl thiocyanateHCID 25135Boron TrichlorideHCID 27373944-Fluoro-3-methylphenolHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 22489889HCID 22489889, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a IM solution of boron trichloride in dichloromethane (48 ml, 48 mmol) was added, in sequence, a solution of 4-fluoro-3-methylphenol (4.44 ml, 40 mmol) in dichloromethane (40 ml), methyl thiocyanate (3.3 ml, 48 mmol) and anhydrous aluminium chloride (5.4 g, 40 mmol) at 0° C. with stirring. The reaction mixture was heated under reflux for 3 h, and stirred at room temperature overnight. The solvent was evaporated, replaced by dichloroethane and added to ice and 4N sodium hydroxide (132 ml). The mixture was heated at reflux for 0.5 h with stirring, cooled to room temperature, the organic layer separated, and the aqueous layer further washed with dichloroethane. The aqueous layer was acidified with 2M hydrochloric acid and the solid that had precipitated collected by filtration, and washed well with water. The solid was dissolved in ethyl acetate, dried over magnesium sulphate, evaporated and the residue triturated with isohexane with ice cooling to give 3.5 g (58%) of the sub title compound as a colourless solid.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 h
  3. customThe solvent was evaporated
  4. additionadded to ice and 4N sodium hydroxide (132 ml)
  5. temperatureThe mixture was heated
  6. temperatureat reflux for 0.5 h
  7. stirringwith stirring
  8. temperaturecooled to room temperature
  9. customthe organic layer separated
  10. washthe aqueous layer further washed with dichloroethane
  11. customthe solid that had precipitated
  12. filtrationcollected by filtration
  13. washwashed well with water
  14. dissolutionThe solid was dissolved in ethyl acetate
  15. dry with materialdried over magnesium sulphate
  16. customevaporated
  17. customthe residue triturated with isohexane with ice cooling

Quellen und Nachweise

ORD-Eintrag
ord-2aacb118455f413a93b0b7f437557c24
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06887871B2

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