Phosphorus oxychloride → methyl 3-chloro-1-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate

HRID 402484

Reaktionsgleichung

Reaktionsgleichung von HRID 402484
O=P(Cl)(Cl)[Cl:3].O[C:7]1[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[N:9]([CH3:16])[N:8]=1>C(Cl)(Cl)Cl>[Cl:3][C:7]1[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[N:9]([CH3:16])[N:8]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178498599HCID 178498599, Verbindung

Produkt 1

HCID 67209560methyl 3-chloro-1-methyl-4,5-dihydro-1H-pyrazole-5-carboxylateAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a solution of POCl3 (31.8 ml, 341 mmol) and Net3 (47.6 ml, 341 mmol) in CHCl3 (100 ml) at −5° C. was added a solution of methyl 3-hydroxy-1-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate (36 g, 228 mmol) in CHCl3 (100 ml). After 1 h at this temperature, the mixture was stirred for another 20 h under warming to rt. Then, the reaction mixture was poured on ice water and extracted with CHCl3. The combined organics were washed with water, dried over Na2SO4 and evaporated under reduced pressure. This yielded the title compound (21 g, 52%) which was used in the next step without further purification. [LCMS RtJ=0.63 min; [M+H]+=177.0, 179.0]

Aufarbeitung

  1. additionThen, the reaction mixture was poured on ice water
  2. extractionextracted with CHCl3
  3. washThe combined organics were washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d744a7b091ec495990d10dac49ef6102
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742106B2

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