Diphenyl Ether → methyl 6-chloro-5-acetamido-2H-chromene-8-carboxylate

HRID 52669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52669
[C:1]([NH:4][C:5]1[C:14]([Cl:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:16][CH2:17][C:18]#[CH:19])[CH:6]=1)(=[O:3])[CH3:2].O(C1C=CC=CC=1)C1C=CC=CC=1>>[C:1]([NH:4][C:5]1[C:6]2[CH:19]=[CH:18][CH2:17][O:16][C:7]=2[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][C:14]=1[Cl:15])(=[O:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 7583Diphenyl EtherHCID 10588933Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate

Produkt 1

HCID 54402287methyl 6-chloro-5-acetamido-2H-chromene-8-carboxylateAusbeute 33,8 %

Reaktionsbedingungen

Temperatur
230 °C

Versuchsvorschrift

A mixture of 40 parts of methyl 4-(acetylamino)-5-chloro-2-(2-propynoxy)benzoate and 172 parts of phenoxybenzene was stirred for 45 min. at 230° C. After cooling, the reaction mixture was poured into petroleumether. The organic layer was separated, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 97:3). The eluent of the desired fractions was evaporated and the residue was crystallized from acetonitrile, yielding 11.9 parts (33.8%) of methyl 5-(acetylamino)-6-chloro-2H-1-benzopyran-8-carboxylate (interm 11).

Aufarbeitung

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into petroleumether
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 97:3)
  8. customThe eluent of the desired fractions was evaporated
  9. customthe residue was crystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-10e04535e1cc4b168e8fc442bfc7115c
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616738

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