Pyrazole → dimethyl 4-(1H-1-pyrazolyl)phthalate

HRID 47314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47314
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.F[C:9]1[CH:10]=[C:11]([C:19]([O:21][CH3:22])=[O:20])[C:12](=[CH:17][CH:18]=1)[C:13]([O:15][CH3:16])=[O:14]>CN1CCCC1=O>[N:3]1([C:18]2[CH:17]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[C:11](=[CH:10][CH:9]=2)[C:19]([O:21][CH3:22])=[O:20])[CH:7]=[CH:6][CH:5]=[N:4]1

Komponenten

5

Edukt 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 22744505Dimethyl 4-fluorobenzene-1,2-dicarboxylate

Produkt 1

HCID 22744587dimethyl 4-(1H-1-pyrazolyl)phthalateAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

26 g of oily sodium hydride was added over 40 min to 200 ml solution of 44 g pyrazole in 1-methyl-2-pyrrolidinone. 125 g of dimethyl 4-fluorophthalate was added thereto over 30 min and stirred at room temperature for 2 hr. The reaction solution was cooled to 0° C. and added to ice water. It was extracted with ethyl acetate, and washed with saturated sodium bicarbonate and brine. It was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated, and diethyl ether was added to the resulting crystalline residue which was then collected by filtration to give 77 g of dimethyl 4-(1H-1-pyrazolyl)phthalate.

Aufarbeitung

  1. temperatureThe reaction solution was cooled to 0° C.
  2. extractionIt was extracted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialIt was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. additiondiethyl ether was added to the resulting crystalline residue which
  8. filtrationwas then collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-5ffa78c552fb4fe1ba846fff5196fa9b
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699870B2

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