Water → 1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazole

HRID 238121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238121
[OH-].[K+].[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Cl.O>CS(C)=O>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][N:5]1[C:4]([CH3:3])=[CH:8][C:7]([CH3:9])=[N:6]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 62103,5-DimethylpyrazoleHCID 119062-Chlorobenzyl chlorideHCID 14797Potassium Hydroxide

Produkt 1

HCID 6618091-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazoleAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Powdered potassium hydroxide (1.751 g, 31.2 mmol) was added to a solution of 3,5-dimethylpyrazole (2 g, 20.81 mmol) in anhydrous DMSO (10.40 ml) and the resulting heterogeneous solution was stirred for 1.5 hr at 80° C. before being cooled to room temperature. 2-Chloro benzylchloride (2.64 ml, 20.81 mmol) was then added in 6 M DMSO over 15 min, and the solution was stirred for a further 1.5 hrs. Upon completion as observed by TLC, the reaction was poured over water and the resulting aqueous phase was extracted with two 20 mL portions of CHCl3. The combined organic layers were washed with 100 mL of water, dried with anhydrous MgSO4 and concentrated under reduced pressure to yield 4.55 g (99%) of 1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazole as a clear liquid. 1H NMR (300 MHz, CDCl3) δ 7.41-7.31 (m, 1H), 7.24-7.09 (m, 2H), 6.59-6.50 (m, 1H), 5.90 (s, 1H), 5.31 (s, 2H), 2.26 (s, 3H), 2.15 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 148.32, 139.96, 135.46, 131.96, 129.42, 128.76, 127.72, 127.48, 105.84, 50.12, 13.80, 11.15. HRMS (m/z): [MNa]+ calc for C12H13ClN2Na+243.07. found 243.0651.

Aufarbeitung

  1. temperaturebefore being cooled to room temperature
  2. stirringthe solution was stirred for a further 1.5 hrs
  3. extractionthe resulting aqueous phase was extracted with two 20 mL portions of CHCl3
  4. washThe combined organic layers were washed with 100 mL of water
  5. dry with materialdried with anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ab4372ff7d8a4d6e927411694a832348
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642614B2

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