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

HRID 570279

Reaktionsgleichung

Reaktionsgleichung von HRID 570279
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([CH3:15])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:19])(=O)=O.O>ClCCl>[C:1]([C:5]1[C:9]([Cl:19])=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([CH3:15])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 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 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A 5-L, four neck round bottom flask equipped with overhead air stirrer, positive pressure nitrogen inlet, thermocouple, and addition funnel was charged with ethyl 3-tert-butyl-1-methyl-1H-pyrazole-5-carboxylate (250 g, 1.19 mol) in dichloromethane (2.5 L). The resulting solution was cooled to 10° C. with a wet-ice bath. Sulfuryl chloride (149 mL, 1.49 mol) was added via addition funnel at such which maintained the temperature between 21-31° C. The resulting mixture was then stirred for 2 h at room temperature. A separate 12-L, four neck flask equipped with overhead air stirrer and thermocouple was charged H2O (3.75 L) and cooled to 10° C. This mixture was then added via addition funnel, while maintaining the temperature below 32° C. and the resulting mixture was stirred for 30 min. The layers were separated, the aqueous layer was extracted with dichloromethane (2×1 L). The organic layer was carefully washed with NaHCO3 (saturated, 2×2 L), brine (1.25 L), dried over Na2SO4, filtered, and evaporated to yield ethyl 3-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylate as a white solid. 1H NMR (CHLOROFORM-d) δ: 4.39 (q, J=7.1 Hz, 2H), 4.07 (s, 3H), 1.29-1.49 (m, 12H)

Aufarbeitung

  1. additionthermocouple, and addition funnel
  2. temperaturemaintained the temperature between 21-31° C
  3. temperaturecooled to 10° C
  4. additionThis mixture was then added via addition funnel
  5. temperaturewhile maintaining the temperature below 32° C.
  6. stirringthe resulting mixture was stirred for 30 min
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with dichloromethane (2×1 L)
  9. washThe organic layer was carefully washed with NaHCO3 (saturated, 2×2 L), brine (1.25 L)
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3a0db9043ed8472ca75e3962ff9f4315
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023846B2

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