Pyridine → 10H-phenothiazine-2-carbothioamide

HRID 1442490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1442490
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:15]([NH2:17])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1.N1C=CC=CC=1>O1CCOCC1>[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:15](=[S:27])[NH2:17]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 87949Lawesson's reagentHCID 2271157510H-phenothiazine-2-carboxamide

Produkt 1

HCID 2271158710H-phenothiazine-2-carbothioamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A reaction mixture comprising 3.4 g (14 mmoles) of 10H-phenothiazine-2-carboxamide (J. Org. Chem. 1961, 26, 1138-1143) and 3.4 g (8.4 mmoles) of Lawesson reagent in solution in 40 ml of 1,4-dioxane to which 20 ml of pyridine has been added is heated to 110° C. for 1 h 30. The brown solution is then concentrated under vacuum and the residue is diluted in 200 ml of AcOEt and 100 ml of H2O. After stirring and decantation, the organic phase is washed successively with 100 ml of a 1N aqueous solution of HCl and 100 ml of salt water. After drying over sodium sulphate, filtration and evaporation of the solvent under vacuum, an orange powder is obtained. This powder is washed with Et2O, the filtrate is eliminated, and extracted with acetone. The acetone filtrate is then concentrated under vacuum and the evaporation residue is then purified using a silica column (eluent: Heptane/AcOEt: 1/1 to 4/6). Orange powder. Melting point: 208-209° C.

Aufarbeitung

  1. concentrationThe brown solution is then concentrated under vacuum
  2. additionthe residue is diluted in 200 ml of AcOEt
  3. washdecantation, the organic phase is washed successively with 100 ml of a 1N aqueous solution of HCl and 100 ml of salt water
  4. dry with materialAfter drying over sodium sulphate, filtration and evaporation of the solvent under vacuum
  5. customan orange powder is obtained
  6. washThis powder is washed with Et2O
  7. extractionextracted with acetone
  8. concentrationThe acetone filtrate is then concentrated under vacuum
  9. customthe evaporation residue is then purified

Quellen und Nachweise

ORD-Eintrag
ord-21ba27b2efa74e05a5bc8292dc67430f
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659266B2

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