Water → 2-(2-Chloro-4-isobutoxyphenoxy)-1,3-thiazole

HRID 404877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404877
[Cl:1][C:2]1[CH:3]=[C:4]([OH:14])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1.[H-].[Na+].[CH2:17](I)[CH:18]([CH3:20])[CH3:19].O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH2:17][CH:18]([CH3:20])[CH3:19])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10556Isobutyl iodide2×HCID 24758Sodium hydride2×HCID 691693943-Chloro-4-(1,3-thiazol-2-yloxy)phenol

Produkt 1

HCID 694334702-(2-Chloro-4-isobutoxyphenoxy)-1,3-thiazoleAusbeute 45,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of Example 9B (3.4 g, 0.015 mol) in N,N-dimethyl formamide was added sodium hydride (0.7 g, 0.018 mol) in portions at room temperature. After stirring for 15 minutes, isobutyl iodide (4.2 g, 0.023 mol) was added rapidly and the mixture was stirred at room temperature for 24 hours. More sodium hydride and isobutyl iodide were added later to complete the reaction. Water was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and purified on silica gel (5˜35% ethyl acetate in hexane) to give 1.92 g of product as clear oil (45% yield), 1H NMR (300 MHz, CDCl3) δ ppm 1.02 (d, J=6.62 Hz, 6H) 1.98-2.18 (m, 1H) 3.71 (d, J=6.62 Hz, 1H) 6.79 (d, J=4.04 Hz, 1H) 6.83 (d, J=2.94 Hz, 1H) 6.86 (d, J=2.94 Hz, 1H) 7.00 (d, J=2.94 Hz, 1H) 7.19 (d, J=4.04 Hz, 1H) 7.24 (s, 1H). MS (ESI) m/z 284.0 (M+H)+.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. customthe reaction
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified on silica gel (5˜35% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b3eb5e506de142bdb95ef1deb93e3bf0
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748627B2

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