Ammonium Chloride → 3,5-Dichloro-3-(2,3-dimethoxyphenyl)-1,3-dihydro-2h-indol-2-one

HRID 983521

Reaktionsgleichung

Reaktionsgleichung von HRID 983521
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])OC(C)(C)C)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[CH3:21][O:22][C:23]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=1[C:31](=O)C(OCC)=O.[NH4+].[Cl-:39]>CCOCC.CCCCC.C1COCC1>[Cl:39][C:31]1([C:24]2[CH:25]=[CH:26][CH:27]=[C:28]([O:29][CH3:30])[C:23]=2[O:22][CH3:21])[C:4]2[C:5](=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[NH:8][C:9]1=[O:15]

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 546372tert-butyl N-(4-chlorophenyl)carbamateHCID 21905960Ethyl 2-(2,3-dimethoxyphenyl)-2-oxoacetateHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 219059313,5-Dichloro-3-(2,3-dimethoxyphenyl)-1,3-dihydro-2h-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

A mixture of 11.4 g of tert-butyl 4-chlorophenylcarbamate in 100 ml of ether is cooled to −40° C. under an atmosphere of dry nitrogen, 80 ml of a 1.5 M solution of tert-butyllithium in pentane are added dropwise and the mixture is left stirring at −20° C. for 3 hours. The reaction mixture is cooled to −40° C., a solution-of 14 g of the compound obtained in step A in 50 ml of THF is added over 1 hour and the mixture is left stirring for 4 days at RT. The reaction mixture is poured into saturated NH4Cl solution and the precipitate formed is spin-filtered off and dried. 10.2 g of the expected product are obtained and are used without further purification in the following step.

Aufarbeitung

  1. waitthe mixture is left
  2. temperatureThe reaction mixture is cooled to −40° C.
  3. waitthe mixture is left
  4. stirringstirring for 4 days at RT
  5. customthe precipitate formed
  6. filtrationis spin-filtered off
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5e48b884da0a4dc68bc38430fdae107f
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06864277B2

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