Trimethylsilyl iodide → 2-tert-Butyl-4-butylisothiazol-5(2H)-imine

HRID 76275

Reaktionsgleichung

Reaktionsgleichung von HRID 76275
[CH2:1]([C:5]1=[CH:6][N:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[S:8]/[C:9]/1=[N:10]\C(=O)OCC)[CH2:2][CH2:3][CH3:4].I[Si](C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:16]([N:7]1[CH:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:9](=[NH:10])[S:8]1)([CH3:19])([CH3:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 87184151ethyl (NZ)-N-(4-butyl-2-tert-butyl-1,2-thiazol-5-ylidene)carbamate

Produkt 1

HCID 668672282-tert-Butyl-4-butylisothiazol-5(2H)-imine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a 250-mL, round-bottomed flask containing a magnetic stir bar were added the product from Example 92A (7.11 g, 25.0 mmol) and chloroform (100 mL). Neat iodotrimethylsilane (Aldrich, 6.25 g, 31.1 mmol) was added. A reflux condenser with nitrogen inlet was attached and a heating mantle was applied. The yellow reaction mixture was heated to 60° C. and stirred overnight. After cooling to room temperature, saturated aqueous sodium bicarbonate solution was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated by rotary evaporator to give a yellow semi-solid. The product was purified by flash chromatography (silica get: 30-90% ethyl acetate in hexanes) to afford the title compound. LC-MS (ESI+) m/z 213 (M+H)+

Aufarbeitung

  1. additionTo a 250-mL, round-bottomed flask containing a magnetic stir bar
  2. customA reflux condenser with nitrogen inlet was attached
  3. temperatureAfter cooling to room temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with dichloromethane (2×50 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporator
  9. customto give a yellow semi-solid
  10. customThe product was purified by flash chromatography (silica get: 30-90% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-01187c9311704c09ac8efecb201fc9bb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835475B2

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