Methyl iodide → [4-[(Z)-C-methylsulfanyl-N-(trimethylsilylmethyl)carbonimidoyl]naphthalen-1-yl]methyl acetate

HRID 1873478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1873478
CI.[C:3]([O:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18](=[S:25])[NH:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:10][CH:9]=1)(=[O:5])[CH3:4].[CH3:26]C(C)([O-])C.[K+]>C1COCC1.COC(C)(C)C>[C:3]([O:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](/[C:18](/[S:25][CH3:26])=[N:19]/[CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:10][CH:9]=1)(=[O:5])[CH3:4]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 58092092(4{[(Trimethylsilyl)methyl]carbamothioyl}naphthalen-1-yl)methyl acetate

Produkt 1

HCID 58092085[4-[(Z)-C-methylsulfanyl-N-(trimethylsilylmethyl)carbonimidoyl]naphthalen-1-yl]methyl acetateAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

To a mixed solution of methyl iodide (0.60 g) and (4{[(trimethylsilyl)methyl]carbamothioyl}naphthalen-1-yl)methyl acetate (1.2 g) in THF (30 ml) was added potassium t-butoxide (0.45 g) gradually, and the mixture was stirred for 20 minutes at the same temperature. The mixture was diluted with t-butyl methyl ether and washed with water and a saturated aqueous brine, subsequently dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, to obtain {4-[(Z)-(methylsulfanyl){[(trimethylsilyl)methyl]imino}methyl]naphthalen-1-yl}methyl acetate (1.1 g).

Aufarbeitung

  1. washwashed with water
  2. dry with materiala saturated aqueous brine, subsequently dried over magnesium sulfate
  3. filtrationAfter filtering the reaction mixture
  4. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2d953f5932fc46c2a8ae6d97f8d737cd
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304371B2

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