O,O-Dipyridin-2-yl carbonothioate → 4-(2-(4-Isothiocyanatophenoxy)pyridin-3-yl)-2-(methylthio)pyrimidine

HRID 252647

Reaktionsgleichung

Reaktionsgleichung von HRID 252647
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[C:10]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1.[C:23](=[S:38])(OC1C=CC=CN=1)OC1C=CC=CN=1>C(Cl)Cl>[N:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C:10]2[C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:21][CH:20]=1)=[C:23]=[S:38]

Komponenten

4

Edukt 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 667319134-{3-[2-(Methylthio)pyrimidin-4-yl]pyridin-2-yloxy}benzeneamine

Produkt 1

HCID 866149574-(2-(4-Isothiocyanatophenoxy)pyridin-3-yl)-2-(methylthio)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A dry 100 ml round bottom flask, under nitrogen, was charged with 4-(3-(2-(methylthio)pyrimidin-4-yl)pyridin-2-yloxy) benzenamine (1.72 g, 5.54 mmol), O,O-dipyridin-2-yl carbonothioate (1.35 g, 5.82 mmol), and DCM (37 ml, 0.15 M). The vessel was closed, kept under nitrogen, and mixture stirred at RT for 18 h. The reaction was diluted with 20 ml DCM and washed with water. The organic layer was collected, dried with Na2SO4, filtered, and concentrated to give 4-(2-(4-isothiocyanatophenoxy)pyridin-3-yl)-2-(methylthio)pyrimidine as a yellow solid. MS m/z=353.0 [M+H]+. Calc'd for C17H12N4OS2: 352.43.

Aufarbeitung

  1. customThe vessel was closed
  2. washwashed with water
  3. customThe organic layer was collected
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-18510a68b2ad4c88bd53eea9c2ff1c02
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868177B2

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