Lawesson's reagent → HCID 178490065, Verbindung

HRID 710525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710525
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([NH:12][NH2:13])=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH3:14][O:15][C:16]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:24][CH2:25][C:26](Cl)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>>[CH3:14][O:15][C:16]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:24][CH2:25][C:26]1[S:38][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[NH:1][CH:2]=[N:3][C:4]=3[CH:9]=2)=[N:12][N:13]=1

Komponenten

4

Edukt 3

HCID 87949Lawesson's reagentHCID 110751782,3-DimethoxyphenylpropionylchlorideHCID 166371191H-benzimidazole-5-carbohydrazide

Produkt 1

HCID 178490065HCID 178490065, Verbindung

Versuchsvorschrift

The compound was synthesized starting from benzimidazol-5-carbohydrazide (176 mg; 1 mmol), TEA (0.153 ml; 1.1 mmol), 2,3-dimethoxyphenylpropionylchloride (228 mg, 1.1 mmol) and Lawesson's reagent (606 mg; 1.5 mmol) as described in method 1; yield: 0.025 g (6.8%); MS m/z: 367.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.07 (t, 2H, 3J=7.9 Hz); 3.38 (t, 2H, 3J=7.9 Hz); 3.73 (s, 3H); 3.79 (s, 3H); 6.84 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 6.91 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 6.98 (t, 1H, 3J=8.3 Hz); 7.71 (d, 1H, 3J=8.3 Hz); 7.77 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 8.12 (d, 1H, 4J=1.7 Hz); 8.37 (s, 1H); HPLC (METHOD [A]): rt 12.03 min (95.8%)

Aufarbeitung

  1. customThe compound was synthesized
  2. customrt 12.03 min (95.8%)

Quellen und Nachweise

ORD-Eintrag
ord-c84bcb437e3f48e0a5bcc2788c46c1e3
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181233B2

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