Dimethylamine, hydrochloride → 2-chloro-N,N-dimethyl-4-nitrobenzamide

HRID 1442643

Reaktionsgleichung

Reaktionsgleichung von HRID 1442643
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].Cl.[CH3:15][NH:16][CH3:17]>C1COCC1.Cl>[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([N:16]([CH3:17])[CH3:15])=[O:5]

Komponenten

5

Edukt 2

HCID 10473Dimethylamine, hydrochlorideHCID 81522Benzoyl chloride, 2-chloro-4-nitro-

Produkt 1

HCID 32645532-chloro-N,N-dimethyl-4-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-chloro-4-nitrobenzoyl chloride Compound 13a1 (7.08 g, 32.2 mmol) and dimethylamine hydrochloride (2.62 g, 32.2 mmol) were combined in THF (50 mL) at 0° C. TEA (8.97 mL, 64.4 mmol) was added and the mixture was heated at reflux for 18 hrs. When the reaction was complete, the mixture was diluted with 1N HCl and extracted with EtOAc. The product was isolated by flash chromatography (30-50% EtOAc/hexane gradient) to provide 2-chloro-N,N-dimethyl-4-nitro-benzamide Compound 13a2 (3.05 g) as a tan solid. MS 229 (MH+).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hrs
  3. extractionextracted with EtOAc
  4. customThe product was isolated by flash chromatography (30-50% EtOAc/hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-6fd098a910c04dc3a2df9164f9949f82
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659284B2

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