Triethylamine → HCID 21090614, Verbindung

HRID 350963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350963
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11](=[O:12])[CH2:10][S:9][C:8]1=S.[N:14]1([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.CCN(CC)CC>C1COCC1.[Hg](Cl)Cl>[N:14]1([C:20]2[CH:21]=[CH:22][C:23]([N:24]=[C:8]3[N:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[C:11](=[O:12])[CH2:10][S:9]3)=[CH:25][CH:26]=2)[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 223458353-(Pyridin-2-yl)-2-sulfanylidene-1,3-thiazolidin-4-one

Produkt 1

HCID 21090614HCID 21090614, VerbindungAusbeute 44,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24085Mercuric ChlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-(2-pyridyl)-2-thioxo-thiazolidin-4-one (1.1 g, 5.3 mmol, 1.0 equiv), prepared as described in J. Chem. Soc. (1956) 1644, was dissolved in 30 ml THF and charged with 4-morpholin-4-yl aniline (0.94 g, 5.28 mmol, 1.0 equiv) and Et3N (1.47 ml, 10.6 mmol, 2.0 equiv). Mercury (II) chloride (1.4 g, 5.28 mmol, 1.0 equiv) was added in one portion as a solid, and the heterogeneous mixture was stirred at ambient temperature overnight. The reaction mixture was filtered through Celite, and the filtrate was partitioned between EtOAc and saturated NH4Cl. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography (40% to 100% EtOAc in hexanes, silica) afforded 0.83 g (44%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 8.70 (m, 1H), 7.90 (m, 1H), 7.37–7.44 (m, 2H), 3.99 (s, 2H), 3.84 (m, 4H), 3.11 (m, 4H); MS (ESI) m/z=355.3 (MH+).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate was partitioned between EtOAc and saturated NH4Cl
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bee518b7a7c5416ca27f0f29db853639
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183302B2

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