Methyl iodide → 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

HRID 1844641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844641
[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:7])=[CH:4][C:3]=1[Cl:16].[C:17](=O)([O-])[O-].[K+].[K+].CI>CC(=O)CC>[CH3:17][S:7][C:6](=[N:8][CH2:9][Si:10]([CH3:12])([CH3:13])[CH3:11])[C:5]1[CH:14]=[CH:15][C:2]([Br:1])=[C:3]([Cl:16])[CH:4]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866857054-bromo-3-chloro-N-trimethylsilanylmethylthiobenzamide

Produkt 1

HCID 668366594-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl esterAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-3-chloro-N-trimethylsilanylmethylthiobenzamide (Example I13) (4.43 g) in butanone (80 ml) was added potassium carbonate (2.73 g) and methyl iodide (1.02 ml). The reaction mixture was stirred at ambient temperature for 20 hours. The reaction mixture was concentrated and the residue purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:5) to give of 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (2.56 g). 1H-NMR (400 MHz, CDCl3): 7.55-7.15 (m, 3H), 3.55 (s, 2H), 1.98 (s, 3H), 0.00 (s, 9H) ppm.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:5)

Quellen und Nachweise

ORD-Eintrag
ord-9a6bbc02d5284deeb5a1a0a9201baa6a
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946447B2

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