Benzoyl isothiocyanate → HCID 59603075, Verbindung

HRID 2068706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068706
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[CH:11][C:12]([Br:16])=[C:13]([NH2:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([N:26]=[C:27]=[S:28])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[C:18]([NH:26][C:27]([NH:15][C:13]1[CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]([CH3:17])=[CH:11][C:12]=1[Br:16])=[S:28])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 68284Benzoyl isothiocyanateHCID 70180235-(Benzyloxy)-2-bromo-4-methylaniline

Produkt 1

HCID 59603075HCID 59603075, VerbindungAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-benzyloxy-2-bromo-4-methyl-phenylamine (0.50 g, 1.71 mmol) in acetone (20 mL) was added benzoylisothiocyanate (0.28 mL, 2.08 mmol) dropwise at room temperature. The resulting reaction mixture was stirred for 30 min. at the same temperature. After completion of reaction (TLC monitoring), acetone was distilled off, the solid residue was stirred in hexane for 5-10 min and then filtered to obtain the desired product as white solid (0.70 g, 88%). 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 5.10 (s, 2H), 7.33 (m, 1H), 7.40 (t, J=7.20 Hz, 2H), 7.48 (d, J=7.60 Hz, 2H), 7.55 (m, 3H), 7.67 (m, 1H), 7.73 (s, 1H), 8.0 (d, J=7.20 Hz, 2H), 11.81 (br s, 1H) and 12.59 (br s, 1H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. distillationwas distilled off
  3. stirringthe solid residue was stirred in hexane for 5-10 min
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-f927e7034b9e4aaca502d349e1e301d1
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299065B2

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