1,2-Dichloroethane → 4,5-difluoro-N-methyl-2-nitrobenzamide

HRID 1887698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887698
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.Cl.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:28][C:26]=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH:28][CH3:26])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 42196304,5-Difluoro-2-nitrobenzoic acidHCID 6364545Methylamine hydrochloride

Produkt 1

HCID 619939344,5-difluoro-N-methyl-2-nitrobenzamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 4,5-difluoro-2-nitrobenzoic acid (1.872 g, 9.22 mmol), methylamine hydrogen chloride (0.75 g, 1.2 eq), EDC (2.12 g, 1.2 eq), HOBt (1.5 g, 1.2 eq) in DMF (20 mL) was added DIEA (5.0 mL, 3.0 eq). The mixture was stirred at room temperature for 15 min. It was concentrated and the crude was dissolved in EtOAc. It was washed with a saturated NaHCO3. The solvent was removed and the crude was purified by silica gel chromatography (20%˜80% EtOAc/Hex) to obtain the desired product 4,5-difluoro-N-methyl-2-nitrobenzamide (1.33 g, isolated yield 67%).

Aufarbeitung

  1. concentrationIt was concentrated
  2. dissolutionthe crude was dissolved in EtOAc
  3. washIt was washed with a saturated NaHCO3
  4. customThe solvent was removed
  5. customthe crude was purified by silica gel chromatography (20%˜80% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-fd3f9e7265604aed877b91aafb4e3ad3
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501763B2

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