Lawesson's reagent → 4-bromo-3-chloro-N-trimethylsilanylmethylthiobenzamide

HRID 1844640

Reaktionsgleichung

Reaktionsgleichung von HRID 1844640
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=O)=[CH:4][C:3]=1[Cl:16].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:26]2)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[S:26])=[CH:4][C:3]=1[Cl:16]

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 668366994-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide

Produkt 1

HCID 866857054-bromo-3-chloro-N-trimethylsilanylmethylthiobenzamideAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide (Example I12) (4.6 g) in toluene (150 ml) was added 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson reagent) (5.8 g). The reaction mixture was stirred at ambient temperature for 30 minutes and then at 110° C. for 1.5 hours. The reaction mixture was concentrated and the residue purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:5) to give 4-bromo-3-chloro-N-trimethylsilanylmethylthiobenzamide (4.64 g). 1H-NMR (400 MHz, CDCl3): 1H-NMR (400 MHz, CDCl3): 7.60 (d, 1H), 7.45 (s, 1H), 7.30 (s, 1H), 7.25 (d, 1H), 3.33 (d, 2H), 0.00 (s, 9H) ppm.

Aufarbeitung

  1. waitat 110° C. for 1.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:5)

Quellen und Nachweise

ORD-Eintrag
ord-e6ed26e2d401498fb0ef9332e4a00962
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946447B2

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