Chloroacetyl chloride → 2-chloro-N-(2-hydroxy-3-nitrophenyl)acetamide

HRID 576071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576071
C(=O)([O-])O.[Na+].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[OH:16].[Cl:17][CH2:18][C:19](Cl)=[O:20].[Cl-].[NH4+]>C(OCC)(=O)C.O>[Cl:17][CH2:18][C:19]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[OH:16])=[O:20]

Komponenten

7

Edukt 4

HCID 6577Chloroacetyl chlorideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 51272912-Amino-6-nitrophenol

Produkt 1

HCID 136462502-chloro-N-(2-hydroxy-3-nitrophenyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydrogen carbonate (6.30 g, 75.0 mmol) and water (75 mL) were added to a solution of 2-amino-6-nitrophenol obtained (5.77 g, 37.5 mmol) in ethyl acetate (75 mL) while cooling in ice, and chloroacetic acid chloride (3.58 mL, 45.0 mmol) was added dropwise thereto. After stirring at room temperature for 1.5 hr, the reaction mixture was cooled in ice, saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1) to afford 2-chloro-N-(2-hydroxy-3-nitrophenyl)acetamide as a pale yellow powder (5.70 g).

Aufarbeitung

  1. temperaturewhile cooling in ice
  2. temperaturethe reaction mixture was cooled in ice
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe desiccant was filtered off
  7. concentrationfollowed by concentration under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-e59b37f77a854fafa3db8bf8f9641c23
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09035059B2

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