Water → 2-(2-Chloro-5-fluoro-benzoylamino)malonic acid diethyl ester

HRID 1027471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1027471
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].Cl.[CH2:13]([O:15][C:16](=[O:24])[CH:17]([NH2:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:14].C(N(CC)CC)C.O>ClCCl>[CH2:21]([O:20][C:18](=[O:19])[CH:17]([NH:23][C:4](=[O:5])[C:3]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:2]=1[Cl:1])[C:16]([O:15][CH2:13][CH3:14])=[O:24])[CH3:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 27575402-Chloro-5-fluorobenzoyl chlorideHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Produkt 1

HCID 671759252-(2-Chloro-5-fluoro-benzoylamino)malonic acid diethyl esterAusbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

A solution of 24.4 g of 2-chloro-5-fluoro-benzoyl chloride in 100 ml of dichloromethane was added dropwise to a solution of 26.8 g of aminomalonic acid diethyl ester hydrochloride and 38.6 ml of triethylamine in 50 ml of dichloromethane with cooling in an ice bath. The reaction mixture was stirred for 2 h while the temperature was maintained at 0-5° C. Then 100 ml of water were added slowly. The phases were separated, and the aqueous phase was extracted twice with 100 ml of dichloromethane. The combined organic phases were dried with sodium sulfate, filtered and evaporated to give 39.3 g of the crude title compound.

Aufarbeitung

  1. temperaturewith cooling in an ice bath
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with 100 ml of dichloromethane
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f706cfbb0b07474a9e820413bb8ea0f3
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735387B2

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