Triethylamine → 2,2,3,3-Tetramethylcyclopropanecarboxylic acid (5-chloro-4-methyl-thiazol-2-yl)-amide

HRID 78418

Reaktionsgleichung

Reaktionsgleichung von HRID 78418
[NH2:1][C:2]1(C)[NH:6][CH:5]=[C:4]([Cl:7])[S:3]1.[CH3:9][C:10]1([CH3:18])[C:12]([CH3:14])([CH3:13])[CH:11]1[C:15](Cl)=[O:16].[CH2:19](N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1.CCOC(C)=O>[Cl:7][C:4]1[S:3][C:2]([NH:1][C:15]([CH:11]2[C:10]([CH3:18])([CH3:9])[C:12]2([CH3:14])[CH3:13])=[O:16])=[N:6][C:5]=1[CH3:19]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 686223502-Amino-5-chloro-2-methyl-thiazole

Produkt 1

HCID 866189062,2,3,3-Tetramethylcyclopropanecarboxylic acid (5-chloro-4-methyl-thiazol-2-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-5-chloro-2-methyl-thiazole (Matsuo, Masaaki; Ogino, Takashi; Igari, Norihiro; Seno, Hachiro; Shimomura, Kyoichi., EP 412404) (150 mg, 0.81 mmol), 2,2,3,3-tetramethylcyclopropanecarbonyl chloride (143 mg, 0.89 mmol), 4-dimethylaminopyridine (50.0 mg, 0.41 mmol) and triethylamine (226 μL, 1.62 mmol) in 15 mL of THF heated at reflux for 48 hours. The mixture was cooled to ambient temperature, diluted with EtOAc and washed with brine. The layers were separated and the aqueous phase was extracted with EtOAc (2×). The combined organic extracts were dried (Na2SO4), filtered, and concentrated. Purification by silica gel chromatography afforded the title compound: MS (LC/MS) m/z 273 (M+H)+.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. washwashed with brine
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with EtOAc (2×)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-82a0aa263bd64a1396aa0534c51643ff
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841334B2

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