Lawesson's reagent → Atb-346

HRID 18632

Reaktionsgleichung

Reaktionsgleichung von HRID 18632
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:13]([CH3:26])[C:14]([O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23](=O)[NH2:24])=[CH:19][CH:18]=3)=[O:15])[CH:9]=2)[CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:13]([CH3:26])[C:14]([O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23](=[S:36])[NH2:24])=[CH:19][CH:18]=3)=[O:15])[CH:9]=2)[CH:4]=1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 593455934-Carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)propanoate2×

Produkt 1

HCID 25065981Atb-346Ausbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4-Carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)-propanoate, 5 (1.80 g, 4.34 mmol) and Lawesson reagent (1.75 g, 4.34 mmol) were dissolved in 130 ml of anhydrous benzene. The reaction was warmed to 60° C. and stirred for 4 h. The solvent was removed under reduced pressure; the crude residue was purified by silica gel column (dichloromethane/methyl alcohol 9.75:0.25) to furnish 2.9 g of crude compound 6. The obtained compound was purified by a silica gel open column and eluted with CH2Cl2/MeOH (9.5/0.5)) giving the pure compound 6 (970 mg, 61% yield).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe crude residue was purified by silica gel column (dichloromethane/methyl alcohol 9.75:0.25)
  3. customto furnish 2.9 g of crude compound 6
  4. customThe obtained compound was purified by a silica gel open column
  5. washeluted with CH2Cl2/MeOH (9.5/0.5))

Quellen und Nachweise

ORD-Eintrag
ord-d78045a97bc94da69a2c6f2ecb99a3ea
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741359B2

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