Pyridine → 2-Chloro-N-[(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyl-sulfanyl-methylene]benzenesulfon-amide

Reaktionsgleichung

[CH2:1]([CH:3]1[CH2:7][NH:6][N:5]=[CH:4]1)[CH3:2].C[S:9][C:10](SC)=[N:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])(=[O:14])=[O:13].N1C=CC=C[CH:25]=1>>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:12]([N:11]=[C:10]([CH3:25])[S:9][N:5]1[CH2:4][CH:3]([CH2:1][CH3:2])[CH:7]=[N:6]1)(=[O:14])=[O:13]

Komponenten

Edukt 3

HCID 1049Pyridine

HCID 4570177HCID 4570177, Verbindung

HCID 59339316HCID 59339316, Verbindung

Produkt 1

HCID 866254122-Chloro-N-[(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyl-sulfanyl-methylene]benzenesulfon-amide

Versuchsvorschrift

500 mg 4-Ethyl-4,5-dihydro-1H-pyrazole was dissolved in 10 mL pyridine. 1.51 g N-(Bis-methylsulfanyl-methylene)-2-chloro-benzenesulfonamide was added and the mixture was refluxed overnight. The mixture was concentrated in vacuo and H2O was added, followed by extraction twice with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude product was purified with flash chromatography (gradient DCM:acetone=100:0 to 95:5) to yield 1.30 g of a yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.02 (t, J=7.5 Hz, 3H), 1.55-1.77 (m, 2H), 2.28 (s, 3H), 3.27-3.39 (m, 1H), 4.13 (dd, J=11.5 and 6.5 Hz, 1H), 4.58 (t, J=11.5 Hz, 1H), 7.16 (d, J=2 Hz, 1H), 7.39 (dt, J=7.5 and 2 Hz, 1H), 7.46 (dt, J=7.5 and 2 Hz, 1H), 7.52 (dd, J=7.5 and 2 Hz, 1H), 8.17 (dd, J=7.5 and 2 Hz, 1H).