Water → ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate

HRID 528787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528787
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1.[Cl:12]N1C(=O)CCC1=O.O>CN(C=O)C>[Cl:12][C:3]1[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:5][NH:6][C:2]=1[CH3:1]

Komponenten

5

Edukt 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 77645Ethyl 5-methyl-1H-pyrazole-3-carboxylate

Produkt 1

HCID 604759ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylateAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of ethyl 5-methyl-1H-pyrazole-3-carboxylate (Maybridge, 4.41 g, 28.6 mmol) in DMF (14 mL) was added N-chlorosuccinimide (3.86 g, 28.9 mmol). The resulting solution was heated at 60° C. for 3 h and then cooled to room temperature. Water was added until a white precipitate formed, and the solid was collected by filtration washing with water. The solid was dissolved in CH2Cl2, washed with water (2×), dried over MgSO4 and concentrated in vacuo to provide the title compound (5.14 g, 90%) as a white solid. 1H NMR (CDCl3) δ 8.03 (s, 1H), 4.42 (q, J=7.0 Hz, 2H), 2.32 (s, 3H), 1.42 (t, J=7.1 Hz, 3H); MS(ESI+) m/z 188.9 (M+H)+.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customformed
  3. filtrationthe solid was collected by filtration
  4. washwashing with water
  5. dissolutionThe solid was dissolved in CH2Cl2
  6. washwashed with water (2×)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-684ff452f35b4f79b29152e27c19e736
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346795B2

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