Pyrithione → 2,2'-Thiodipyridine

HRID 979409

Reaktionsgleichung

Reaktionsgleichung von HRID 979409
[C:1](Cl)(=O)[C:2](Cl)=O.[Na].O[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=[S:15]>C1C=CC=CC=1.CN(C=O)C.CN(C1C=CN=CC=1)C>[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15][C:2]1[CH:1]=[CH:12][CH:11]=[CH:10][N:9]=1

Komponenten

7

Edukt 3

HCID 1570PyrithioneHCID 65578Oxalyl chlorideHCID 5360545Sodium

Produkt 1

HCID 5211142,2'-ThiodipyridineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

360 mg (1 mmol) of peracetoquinic acid (32) are taken into solution with stirring in 5 ml of benzene with the addition of 1 ml of oxalyl chloride and 1 drop of DMF for 3 hours. After evaporation to dryness, the residue is taken up in 5 ml of benzene and added with stirring to a suspension of 180 mg (1.1 mmol) of the sodium salt of N-hydroxypyridine-2-thione and 12 mg (0.1 mmol) of DMAP. The reaction mixture is kept refluxing in 10 ml of toluuene under an atmosphere of nitrogen. After 2 hours of heating under reflux, the cooled reaction mixture is filtered on Celite and evaporated to dryness. By flash chromatography on silica (90% of CH2Cl2 ; 10% EtOAc), 306 mg of pyridyl sulfide of formula (34) are obtained in the form of a yellowish oil. Yield 72%.

Aufarbeitung

  1. customAfter evaporation to dryness
  2. additionadded
  3. temperatureThe reaction mixture is kept refluxing in 10 ml of toluuene under an atmosphere of nitrogen
  4. temperatureAfter 2 hours of heating
  5. temperatureunder reflux
  6. customthe cooled reaction mixture
  7. filtrationis filtered on Celite
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f97cda4dac004f19a4353661f6288300
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04668356

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