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

HRID 2416950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2416950
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-difluoroaniline (1.29 g, 10 mmols) and bromoacetic acid (2.08 g, 15 =mmols), and stirred at room temperature for 12 hours. The reaction mixture was extracted with other. 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 other
  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-5b71920e1a6c4cf3ac1ae839f714e274
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825223B2

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