Diethyl Ether → 4'-Dimethylaminoacetanilide

HRID 523867

Reaktionsgleichung

Reaktionsgleichung von HRID 523867
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH3:8][N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.CCOCC>C(Cl)Cl>[C:5]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([N:9]([CH3:17])[CH3:8])=[CH:11][CH:12]=1)(=[O:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 7472N,N-dimethyl-p-phenylenediamineHCID 7918Acetic Anhydride

Produkt 1

HCID 819684'-DimethylaminoacetanilideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of acetic anhydride (11.5 mL, 12.45 g, 0.122 mol) in anhydrous CH2Cl2 (100 mL) was added N,N-dimethyl-1,4-phenylenediamine (11.37 g; 83.5 mmol) portion-wise over 30 min at 0° C. The mixture was allowed to gradually warm to room temperature and stirred for 24 hours. The solvent was removed under high vacuum to obtain a black residue which was stirred with Et2O (20 mL) at room temperature. The suspension was filtered and the solid washed with Et2O (3×20 mL). The solid residue was dried under high vacuum to obtain the intermediate N-acetyl-N′,N′-dimethyl-1,4-phenylenediamine as a black solid (12.8 g, 86%) which was used in the next step without further purification.

Aufarbeitung

  1. customThe solvent was removed under high vacuum
  2. customto obtain a black residue which
  3. filtrationThe suspension was filtered
  4. washthe solid washed with Et2O (3×20 mL)
  5. customThe solid residue was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8fe6959594ae47a78180183b92f8aedb
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340498B2

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