Methanol → 1-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrole-2-carbaldehyde

HRID 252005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252005
CO.[Cl:3][C:4]1[C:5]([N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[CH:15]=[O:16])=[N:6][CH:7]=[CH:8][CH:9]=1.[S-:17][C:18]#[N:19].[Na+].BrBr>[Br-].[Na+].CO>[Cl:3][C:4]1[C:5]([N:10]2[C:14]([S:17][C:18]#[N:19])=[CH:13][CH:12]=[C:11]2[CH:15]=[O:16])=[N:6][CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24408BromineHCID 516871Sodium thiocyanateHCID 587620783-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine

Produkt 1

HCID 866325621-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrole-2-carbaldehydeAusbeute 125,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 20267117Sodium bromide methanolLösungsmittel

Versuchsvorschrift

To 10 ml of methanol were added 1.0 g of 3-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine and 1.4 g of sodium thiocyanate. A solution of 1.0 g of bromine in 5 ml of saturated sodium bromide-methanol was added dropwise thereto at −20° C. The resulting mixture was stirred at the same temperature for 2 hours. The reaction mixture was added to 100 ml of ice water, and extracted with chloroform two times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 1.6 g of 1-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrole-2-carbaldehyde of the formula:

Aufarbeitung

  1. customat −20° C
  2. extractionextracted with chloroform two times
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-04403b1700a844b48fe01341652056e6
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07867949B2

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