2-Aminothiazole → 2,2,3,3-tetramethyl-N-1,3-thiazol-2-ylcyclopropanecarboxamide

HRID 78395

Reaktionsgleichung

Reaktionsgleichung von HRID 78395
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH3:7][C:8]1([CH3:16])[C:10]([CH3:12])([CH3:11])[CH:9]1[C:13](Cl)=[O:14].C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl.O>[CH3:7][C:8]1([CH3:16])[C:10]([CH3:12])([CH3:11])[CH:9]1[C:13]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)=[O:14]

Komponenten

7

Edukt 3

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

Produkt 1

HCID 7224802,2,3,3-tetramethyl-N-1,3-thiazol-2-ylcyclopropanecarboxamideAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a solution of 2-aminothiazole (0.39 g, 3.9 mmol) in 10 mL of methylene chloride at 0° C. was added a solution of the product from Example 1A in 8 mL of chloroform, followed by triethylamine (1.0 mL, 7.7 mmol). The mixture was stirred for 7 hours at 35° C., cooled to ambient temperature and diluted with water. The phases were separated and the aqueous phase was extracted with methylene chloride. The combined organic extracts were washed twice with water and then brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by column chromatography (SiO2, 30-60% ethyl acetate/hexanes gradient) afforded 0.11 g (14%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.18 (s, 1H), 1.25 (s, 6H), 1.35 (s, 6H), 6.92 (d, J=3.4 Hz, 1H), 7.39 (d, J=3.4 Hz, 1H), 10.7 (s, 1H); MS (DCI/NH3) m/z 225 (M+H)+. Anal. Calculated for C11H16N2OS: C, 58.90; H, 7.19; N, 12.49. Found: C, 59.03; H, 7.34; N, 12.34.

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with methylene chloride
  4. washThe combined organic extracts were washed twice with water
  5. dry with materialbrine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (SiO2, 30-60% ethyl acetate/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-816269fbd7084bc4a5013b91d290c72b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841334B2

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