2,6-Dichlorobenzaldehyde → (3-Chloro-1,1-dimethylpropyl)-(2,6-dichlorobenzylidene)-amine

HRID 1350912

Reaktionsgleichung

Reaktionsgleichung von HRID 1350912
Cl.[Cl:2][CH2:3][CH2:4][C:5]([NH2:8])([CH3:7])[CH3:6].[OH-].[Na+].[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:13]=1[CH:14]=O>C(Cl)Cl>[Cl:2][CH2:3][CH2:4][C:5]([N:8]=[CH:14][C:13]1[C:12]([Cl:11])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:20])([CH3:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 67372,6-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 21094547686746-12-3

Produkt 1

HCID 21094546(3-Chloro-1,1-dimethylpropyl)-(2,6-dichlorobenzylidene)-amineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

13.3 g (84.0 mmol) of 3-chloro-1,1-dimethyl propylamine-hydrochloride were added to 84.0 mL sodium hydroxide solution (1 M) at 0° C. with vigorous stirring. The reaction mixture was stirred for 30 min at 0° C. and then combined with 50 mL methylene chloride. The phases were separated and the aqueous phase was twice extracted with 35 mL methylene chloride. The combined organic phases were dried over magnesium sulphate and at ambient temperature combined with 14.2 g (81.0 mmol) of 2,6-dichlorobenzaldehyde with stirring. The reaction mixture was stirred for 18 h at ambient temperature, dried again with magnesium sulphate and the solvent was removed. 22.3 g (80.0 mmol, 99%) (3-chloro-1,1-dimethylpropyl)-(2,6-dichlorobenzylidene)-amine were obtained as a yellowish oil.

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous phase was twice extracted with 35 mL methylene chloride
  3. dry with materialThe combined organic phases were dried over magnesium sulphate and at ambient temperature
  4. stirringwith stirring
  5. stirringThe reaction mixture was stirred for 18 h at ambient temperature
  6. dry with materialdried again with magnesium sulphate
  7. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-97b6c5badb5e4b48ab2cce294e41862e
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214698B2

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