Chloroacetyl chloride → 2-chloro-N-(3,5-dimethylphenyl)acetamide

HRID 490162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490162
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].[Cl:10][CH2:11][C:12](Cl)=[O:13]>[OH-].[Na+].ClCCl>[Cl:10][CH2:11][C:12]([NH:5][C:4]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:2]([CH3:1])[CH:3]=1)=[O:13]

Komponenten

5

Edukt 2

HCID 6577Chloroacetyl chlorideHCID 79493,5-Dimethylaniline

Produkt 1

HCID 15228732-chloro-N-(3,5-dimethylphenyl)acetamideAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

3,5-Dimethylaniline (Acros, 10.50 mL, 84.05 mmol) in 2N sodium hydroxide (200 mL) was treated with chloroacetyl chloride (Acros, 10.00 mL, 125.7 mmol) as a solution in dichloromethane (200 mL) drop wise. After 18 hours, the layers were separated. The organic phase was washed with 1N hydrochloric acid, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide 15.64 g (94%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.24 (s, 6H), 4.21 (s, 2H), 6.73 (s, 1H), 7.20 (s, 2H), 10.11 (br s, 1H); MS (DCI/NH3) m/e 198 (M+H)+.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic phase was washed with 1N hydrochloric acid
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-225bfdf6b3b7427dbf7feea6fd7d478b
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528134B2

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