Ethoxalyl chloride → Ethyl 2-(4-chloro-3-fluorophenylamino)-2-oxoacetate

HRID 626609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626609
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].Cl[C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(Cl)Cl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][C:3]=1[F:9]

Komponenten

4

Edukt 2

HCID 20884Ethoxalyl chlorideHCID 27365114-Chloro-3-fluoroaniline

Produkt 1

HCID 57523348Ethyl 2-(4-chloro-3-fluorophenylamino)-2-oxoacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

TEA (2.28 g, 0.023 mol) was added at once to a solution of 3 g (0.0206 mol) 4-chloro-3-fluoroaniline in 50 ml of DCM and then ethyl 2-chloro-2-oxoacetate (2.81 g, 0.0206 mol) was added dropwise at 0° C. Reaction mixture was stirred at 0° C. for 1 h and then continued at room temperature (RT) for 6 h. The mixture was washed with 25% aqueous solution of K2CO3 (2×50 ml) and water (50 ml). The product was dried over Na2SO4 and evaporated. The residue was washed with ether and dried on the air to give ethyl 2-(4-chloro-3-fluorophenylamino)-2-oxoacetate (2′) (3.97 g, 78.6%) as a white powder; LC-MS (APCI+) m/z: calcd for C18H8CIFNO3: 245.03. found: 245 (M+H+).

Aufarbeitung

  1. customReaction mixture
  2. customcontinued at room temperature
  3. custom(RT)
  4. customfor 6 h
  5. washThe mixture was washed with 25% aqueous solution of K2CO3 (2×50 ml) and water (50 ml)
  6. dry with materialThe product was dried over Na2SO4
  7. customevaporated
  8. washThe residue was washed with ether
  9. customdried on the air

Quellen und Nachweise

ORD-Eintrag
ord-1a5f8bac1e57414091643d19ac1386c4
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309237B2

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