Lawesson's reagent → 2H-1-Benzazepine-2-thione, 1,3,4,5-tetrahydro-7-(3-pyridinyl)-

HRID 1521576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521576
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]3[NH:16][C:15](=O)[CH2:14][CH2:13][CH2:12][C:11]=3[CH:18]=2)[CH:2]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:28]2)=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]3[NH:16][C:15](=[S:28])[CH2:14][CH2:13][CH2:12][C:11]=3[CH:18]=2)[CH:2]=1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 44480908HCID 44480908, Verbindung

Produkt 1

HCID 899616802H-1-Benzazepine-2-thione, 1,3,4,5-tetrahydro-7-(3-pyridinyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

The title compound from Example 2 Step D (0.200 g, 0.839 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane2,4-disulfide (0.255 g, 0.629 mmol) were suspended in toluene (1.7 mL) and then heated to reflux for several hours. The reaction solution was then cooled to room temperature and concentrated. Purification by flash chromatography on silica gel (0-10% methanol in ethyl acetate) provided the title compound: LCMS m/z 255.03 [M+H]+; 1H NMR (500 MHz, d6-DMSO) δ 8.81 (s, 1H), 8.48-8.47 (m, 1H), 8.02 (d, J=7.9 Hz, 1H), 7.58-7.56 (m, 2H), 7.42 (dd, J=4.8, 7.9 Hz, 1H), 7.13 (d, J=8.1 Hz, 1H), 2.74-2.71 (m, 2H), 2.68-2.65 (m, 2H), 2.26-2.20 (m, 2H).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for several hours
  3. concentrationconcentrated
  4. customPurification by flash chromatography on silica gel (0-10% methanol in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2cac286383844eedb65fa7ebd8fe3a95
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

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