2-Chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamide → HCID 178492991, Verbindung

HRID 1627359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1627359
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:26])([C:10](=O)[CH2:11][NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([O:23][CH3:24])[CH:17]=2)=[S:14])[CH3:9])[CH:5]=[CH:4][C:3]=1[S:27]([NH2:30])(=[O:29])=[O:28]>CC(O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([O:23][CH3:24])[CH:17]=3)[C:13]([SH:14])=[N:12][CH:11]=2)([CH3:26])[CH3:9])[CH:5]=[CH:4][C:3]=1[S:27]([NH2:30])(=[O:29])=[O:28]

Komponenten

3

Edukt 1

HCID 866622522-Chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamide

Produkt 1

HCID 178492991HCID 178492991, VerbindungAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamide (8.6 g, 18.1 mmol) in AcOH (100 mL) was refluxed 3 h. After the reaction was complete, the solution was cooled to room temperature and azeotroped with toluene. The residue was triturated with Et2O, filtered and dried to provide the title compound (6.8 g, 82% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3+MeOD) δ 7.92 (d, J=8.4 Hz, 1H), 7.09 (s, 1H), 7.06 (d, J=8.4 Hz, 1H), 6.97 (t, J=8.4 Hz, 1H), 6.89 (s, 1H), 6.38 (m, 1H), 6.13 (d, J=7.2 Hz, 1H), 3.58 (s, 3H), 1.54 (s, 6H); MS (EI) m/z 456 (MH+).

Aufarbeitung

  1. customazeotroped with toluene
  2. customThe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-05aff3d08e264a2b93b7bf68043f802e
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785488B2

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