Triethylamine → methyl (E)-2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-acrylate

HRID 2116686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2116686
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:24]1[CH:30]=[C:29]([CH3:31])[C:27]([NH2:28])=[C:26]([Cl:32])[CH:25]=1.[C:33]([NH:36][C:37](=[CH2:42])[C:38]([O:40][CH3:41])=[O:39])(=[O:35])[CH3:34].C(N(CC)CC)C>C(#N)C>[C:33]([NH:36]/[C:37](=[CH:42]/[C:24]1[CH:30]=[C:29]([CH3:31])[C:27]([NH2:28])=[C:26]([Cl:32])[CH:25]=1)/[C:38]([O:40][CH3:41])=[O:39])(=[O:35])[CH3:34]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 98644Methyl 2-acetamidoacrylateHCID 27696264-Bromo-2-chloro-6-methylaniline

Produkt 1

HCID 69363659methyl (E)-2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-acrylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under protective nitrogen gas 2.02 g (9.0 mmol) palladium(II)acetate and 2.82 g (9.0 mmol) tri-o-tolylphosphine were added to a mixture of 25.0 g (113 mmol) 4-bromo-2-chloro-6-methyl-aniline, 19.9 g (136 mmol) methyl 2-acetamidoacrylate, 350 ml triethylamine and 150 ml acetonitrile at ambient temperature. The reaction mixture was stirred for 18 hours at 80° C., evaporated down under reduced pressure, the residue was combined with 600 ml dichloromethane and water and filtered off from the insoluble precipitate. The organic phase was dried over sodium sulphate, evaporated down under reduced pressure and then combined with 200 ml of ethyl acetate/cyclohexane (3/1). The insoluble fraction was suction filtered and the mother liquor was purified by column chromatography through silica gel. The corresponding fractions were evaporated down under reduced pressure and combined with the insolublen fraction suction filtered previously.

Aufarbeitung

  1. customevaporated down under reduced pressure
  2. filtrationfiltered off from the insoluble precipitate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated down under reduced pressure
  5. filtrationfiltered
  6. customthe mother liquor was purified by column chromatography through silica gel
  7. customThe corresponding fractions were evaporated down under reduced pressure
  8. filtrationfiltered previously

Quellen und Nachweise

ORD-Eintrag
ord-19903001339744e3bed1780a61a27394
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439237B2

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