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

Reaction equation

[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]

Participants

Reactant 3

HCID 1049Pyridine

HCID 4570177HCID 4570177, compound

HCID 59339316HCID 59339316, compound

Product 1

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

Procedure

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).