1,1'-Thiocarbonyldiimidazole → 2(1H)-Pyrimidinethione, tetrahydro-1-phenyl-

HRID 1250876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1250876
[C:1]1([NH:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[S:13]>ClCCl>[C:1]1([N:7]2[CH2:8][CH2:9][CH2:10][NH:11][C:12]2=[S:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 427260N-(3-aminopropyl)aniline

Produkt 1

HCID 101980352(1H)-Pyrimidinethione, tetrahydro-1-phenyl-Ausbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Prepared in the manner of Example 1, Step B from N-phenyl-propane-1,3-diamine of Step A and 1,1′-thiocarbonyldiimidazole, except that the cyclization was effected in dichloromethane. Workup consisted of washing with water, drying over magnesium sulfate, filtration and removal of solvent in vacuo. Purfication by flash chromatography on silica gel Merck-60 eluting with 1% methanol in dichloromethane followed by trituration with ethyl ether to provide the title compound as a white solid (2.74 g, 78%), m.p: 211-212° C., identical to the material described by Kashima et al., J. Chem. Soc. Perkin I, 1622 (1981).

Aufarbeitung

  1. washof washing with water
  2. dry with materialdrying over magnesium sulfate, filtration and removal of solvent in vacuo
  3. washeluting with 1% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-1b0acefd610e43ee866e404e4b3a2777
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06340687B1

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