Sulfuryl chloride → ethyl 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylate

HRID 570183

Reaktionsgleichung

Reaktionsgleichung von HRID 570183
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:15])[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)=[O:5])[CH3:2].S(Cl)([Cl:19])(=O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:15])[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:10]=1[Cl:19])=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 24648Sulfuryl chlorideHCID 2799344ethyl 3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxylate

Produkt 1

HCID 67412028ethyl 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-tert-butyl-2-methyl-pyrazole-3-carboxylic acid ethyl ester (2.10 g, 10.0 mmol) in 25 mL of DCM was added sulfuryl chloride (1.05 mL, 13.0 mmol) slowly under Ar. After stirring at room temperature for 3 h under Ar, the resulting mixture was treated with DCM (30 mL), washed with ice H2O, saturated aqueous NaHCO3 and brine, and dried with Na2SO4. Removal of the solvent under reduced pressure yielded the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 4.40 (q, J=7.2 Hz, 2H), 4.07 (s, 3H), 1.42 (t, J=7.2 Hz, 3H), 1.40 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C11H17ClN2O2: 245.1 (M+H), Measured: 245.1.

Aufarbeitung

  1. washwashed with ice H2O, saturated aqueous NaHCO3 and brine
  2. dry with materialdried with Na2SO4
  3. customRemoval of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5f61c25fc0fd4378b046af5a34fad283
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023846B2

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