Ethyl 4-chloroacetoacetate → HCID 19993697, Verbindung

HRID 345119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 345119
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:7]=1[NH2:8].[Cl:18][CH2:19][C:20](=[O:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C([O-])(=O)C.[Na+]>S(=O)(=O)(O)O.C(O)(=O)C.O>[Cl:5][C:6]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:7]=1[N:8]=[N:1][CH:21]([C:20]([CH2:19][Cl:18])=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Komponenten

8

Edukt 4

HCID 69484Ethyl 4-chloroacetoacetateHCID 1410944-Amino-3,5-dichlorobenzotrifluorideHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Produkt 1

HCID 19993697HCID 19993697, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittel2×HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

Sodium nitrite (9.6 g) was warmed in concentrated sulfuric acid (40 ml) to form a homogeneous mixture. The solution was allowed to cool to room temperature and a solution of 2,6-dichloro-4-trifluoromethylaniline (described in European Patent Publication 23,100:30.0 g) in glacial acetic acid (230 ml) was added dropwise, with stirring and efficient external cooling to keep the temperature below 30° C. The reaction mixture was heated at 55°-60° C. for 45 minutes, allowed to cool to room temperature, and added dropwise to a stirred solution of ethyl 4-chloroacetoacetate 21.6 g) in glacial acetic acid (100 ml) and water (200 ml). Sodium acetate (122 g) and a further 200 ml of water were added. The resultant precipitate was filtered and the filter cake was washed thoroughly with water, sucked dry and dried in a vacuum desiccator to give ethyl 2-(2,6-dichloro-4-trifluoromethylphenylazo)-4-chloroacetoacetate as a light brow solid (52.7 g), m.p. 62°-67° C.

Aufarbeitung

  1. customto form a homogeneous mixture
  2. temperatureefficient external cooling
  3. customthe temperature below 30° C
  4. temperatureThe reaction mixture was heated at 55°-60° C. for 45 minutes
  5. temperatureto cool to room temperature
  6. filtrationThe resultant precipitate was filtered
  7. washthe filter cake was washed thoroughly with water
  8. customsucked dry
  9. customdried in a vacuum desiccator

Quellen und Nachweise

ORD-Eintrag
ord-42346639d9c2467091f12bbc1e5033de
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05055482

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