Chlorosuccinimide → 2-chloro-N,N-dimethyl-3-nitro-aniline

HRID 352462

Reaktionsgleichung

Reaktionsgleichung von HRID 352462
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[Cl:13]N1C(=O)CCC1=O>CN(C=O)C>[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[Cl:13]

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 69269N,N-Dimethyl-3-nitroaniline

Produkt 1

HCID 227123482-chloro-N,N-dimethyl-3-nitro-anilineAusbeute 101,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

25 g of N,N-dimethyl-3-nitroaniline is dissolved in 225 ml of DMF. 20 g of N-chlorosuccinimide dissolved in 190 ml of DMF is slowly added dropwise and the solution is stirred at RT. After 24 hours, the solvent is evaporated. About 500 ml of ice is added to the red residue. The suspension is extracted three times with about 200 ml of diethylether. The ether phases are dried over Na2SO4, filtered, and evaporated down. 30.4 g of N,N-dimethyl-2-chloro-3-nitroaniline is obtained as a red oil. The crude product is used further without any additional purification.

Aufarbeitung

  1. additionis slowly added dropwise
  2. customthe solvent is evaporated
  3. additionAbout 500 ml of ice is added to the red residue
  4. extractionThe suspension is extracted three times with about 200 ml of diethylether
  5. dry with materialThe ether phases are dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-6ec2464b864f4df392236929417f9e8e
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747051B2

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