Methylamine → 5-Bromo-2-ethoxy-N,4-dimethylbenzamide

HRID 1295922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295922
[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]([O:11][CH2:12][CH3:13])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:15][NH2:16].C(OCC)(=O)C>O1CCCC1.C(N(CC)CC)C.ClC(OCC)=O>[CH3:15][NH:16][C:7](=[O:8])[C:6]1[CH:10]=[C:2]([Br:1])[C:3]([CH3:14])=[CH:4][C:5]=1[O:11][CH2:12][CH3:13]

Komponenten

7

Edukt 3

HCID 6329MethylamineHCID 8857Ethyl AcetateHCID 22929762HCID 22929762, Verbindung

Produkt 1

HCID 229298455-Bromo-2-ethoxy-N,4-dimethylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 10928Ethyl chloroformateLösungsmittel

Versuchsvorschrift

After dissolving 5-bromo-2-ethoxy-4-methylbenzoic acid in tetrahydrofuran (80 ml), triethylamine (3.5 ml) and ethyl chloroformate (2.4 ml) were added while cooling on ice, the mixture was stirred for 1 hour, and then a 40% methylamine aqueous solution (3.5 ml) was added. The reaction mixture was stirred for 1 hour, ethyl acetate was added and the mixture was washed with brine, after which the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The crystals of the residue were washed with hexane and filtered to yield the title compound (5.08 g) as white crystals.

Aufarbeitung

  1. additionwere added
  2. temperaturewhile cooling on ice
  3. stirringThe reaction mixture was stirred for 1 hour
  4. washthe mixture was washed with brine
  5. dry with materialafter which the organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. washThe crystals of the residue were washed with hexane
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-5de0f3fe9e4c45a9924d44fcaebdefbe
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244730B2

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