Potassium Carbonate → HCID 11611908, Verbindung

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Reaktionsgleichung

Cl[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:20])[CH3:19])[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[CH3:24][C:25]1[CH:26]=[C:27]([SH:32])[CH:28]=[CH:29][C:30]=1[CH3:31].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:24][C:25]1[CH:26]=[C:27]([S:32][C:2]2[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]3[CH2:17][CH2:16][N:15]([C:18](=[O:20])[CH3:19])[CH2:14][CH2:13]3)=[O:11])=[CH:4][C:3]=2[N+:21]([O-:23])=[O:22])[CH:28]=[CH:29][C:30]=1[CH3:31]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of the compound of Example 32A (40 mg, 0.12 mmole) in 2.5 mL of dimethylformamide was added 3,4-dimethylthiophenol (17 mg, 0.12 mmole), followed by potassium carbonate powder (20 mg, 0.14 mmole). The mixture was heated at 100° C. for 20 h. The solvent was removed using N2 gas flow. Water (5 mL) was then added to the residue, the resulting precipitate was collected through filtration, washed with cold water, and air dried to give the title compound (42 mg, 81%) as light yellow solid. 1H-NMR (CDCl3, 400 MHz) δ 2.08 (s, 3H), 2.23 (s, 3H), 2.27 (s, 3H), 3.45 (br, m, 2H), 3.63 (br, m, 6H), 6.79 (s, 1H), 6.82 (d, J=19 Hz, 1H), 7.18 (d, J=19 Hz, 1H), 7.24 (dd, J=4, 19 Hz, 1H), 7.27 (s, 1H), 7.34 (d, J=21 Hz, 1H), 7.56 (d, J=39 Hz, 1H), 8.32 (d, J=4 Hz, 1H). MS (APCI) (M+H)+ at m/z 440. FAB High Resolution MS calculated m/z for C23H26N3O4S (M+H)+: 440.1644. Observed m/z: 440.1646.

Aufarbeitung

customThe solvent was removed
additionWater (5 mL) was then added to the residue
filtrationthe resulting precipitate was collected through filtration
washwashed with cold water, and air
customdried

Quellen und Nachweise

ORD-Eintrag: ord-2f84113fb29943a7863b77b480112481
Quelldatensatz: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06867203B2

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