Isothiocyanatotrimethylsilane → HCID 86684679, Verbindung

HRID 75541

Reaktionsgleichung

Reaktionsgleichung von HRID 75541
[CH3:1][O:2][C:3]1[C:8](/[C:9](/[NH:16][CH2:17][CH2:18][OH:19])=[CH:10]/[C:11]([O:13]CC)=O)=[CH:7][CH:6]=[C:5]([O:20][CH3:21])[N:4]=1.C[Si]([N:26]=[C:27]=[S:28])(C)C>CC1OCCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:8]([C:9]2[N:16]([CH2:17][CH2:18][OH:19])[C:27](=[S:28])[NH:26][C:11](=[O:13])[CH:10]=2)=[CH:7][CH:6]=[C:5]([O:20][CH3:21])[N:4]=1

Komponenten

5

Edukt 2

HCID 75297IsothiocyanatotrimethylsilaneHCID 86684678HCID 86684678, Verbindung

Produkt 1

HCID 86684679HCID 86684679, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 73012-MethyltetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of (Z)-ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-((2-hydroxyethyl)amino)acrylate (100 mg, 0.34 mmol) in 2-MeTHF (1.0 mL) was added (trimethylsilyl)isothiocyanate (0.30 mL, 2.0 mmol) and the reaction mixture was heated at 80° C. for 4 hours. The cooled reaction mixture was diluted with EtOAc and washed with a saturated aqueous sodium bicarbonate solution. The layers were separated and the organic layer was concentrated in vacuo. The residue was triturated with MeOH and the resulting solids were collected by vacuum filtration to give the title compound (16 mg, 16%) as a white solid.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. washwashed with a saturated aqueous sodium bicarbonate solution
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated in vacuo
  5. customThe residue was triturated with MeOH
  6. filtrationthe resulting solids were collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-57d982c63b564ccf8f14e28d8af23c19
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835449B2

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