Bromoacetic Acid → 2-bromo-N-(2,4-difluorophenyl)acetamide

HRID 1532706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1532706
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[F:22][C:23]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:24]=1[NH2:25].[Br:31][CH2:32][C:33](O)=[O:34]>CN(C=O)C>[Br:31][CH2:32][C:33]([NH:25][C:24]1[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:23]=1[F:22])=[O:34]

Komponenten

6

Edukt 4

HCID 6227Bromoacetic AcidHCID 97092,4-DifluoroanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole

Produkt 1

HCID 34164012-bromo-N-(2,4-difluorophenyl)acetamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

WSC (2.1 g, 11 mmols) and HOBt (1.49 g, 11 mmols) were added to a DMF (30 ml) solution of 2,4-difluroaniline (1.29g, 10 mmols) an bromoacetic acid (2.08 g, 15 mmols), and stirred at room temperature for 12 hours. The reaction mixture was extracted with ether. The organic layer was washed with water, 1 N HCl, an aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate, and the solvent was evaporated. Then, the residue was purified through silica gel column chromatography (developer: hexane/acetone=5/1), and the resulting crystals were recrystallized from ether-hexane to obtain 1.7 g (yield: 68%) of 2-bromo-N-(2,4-difluorophenyl)acetamide as colorless needle-like crystals.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with ether
  2. washThe organic layer was washed with water, 1 N HCl
  3. dry with materialan aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThen, the residue was purified through silica gel column chromatography (developer: hexane/acetone=5/1)
  6. customthe resulting crystals were recrystallized from ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-1ecec5b76efc4bbeab419716b55e50ec
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06204278B1

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