Veratroyl chloride → N-[2-chloro-5-(3-dimethylaminobenzamido)4-fluorophenyl]-3,4-dimethoxybenzamide

HRID 991429

Reaktionsgleichung

Reaktionsgleichung von HRID 991429
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[NH2:14][C:15]1[C:16]([Cl:34])=[CH:17][C:18]([F:33])=[C:19]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:31])[CH3:30])[CH:24]=2)[CH:20]=1>N1C=CC=CC=1>[Cl:34][C:16]1[CH:17]=[C:18]([F:33])[C:19]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:30])[CH3:31])[CH:24]=2)=[CH:20][C:15]=1[NH:14][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1

Komponenten

4

Edukt 2

HCID 77070Veratroyl chlorideHCID 22732310N-(5-amino-4-chloro-2-fluorophenyl)-3-dimethylaminobenzamide

Produkt 1

HCID 9847600N-[2-chloro-5-(3-dimethylaminobenzamido)4-fluorophenyl]-3,4-dimethoxybenzamideAusbeute 27,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 3,4-dimethoxybenzoyl chloride (0.5 g), N-(5-amino-4-chloro-2-fluorophenyl)-3-dimethylaminobenzamide (0.781 g) and pyridine (8 ml) was stirred at ambient temperature for 18 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and a saturated aqueous copper sulphate solution. The organic phase was washed in turn with water and a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica using a 99:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound as a solid (0.328 g);

Aufarbeitung

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. washThe organic phase was washed in turn with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica using
  7. additiona 99:1 mixture of methylene chloride and methanol as eluent

Quellen und Nachweise

ORD-Eintrag
ord-206ad1cdf15246a18208d54689358a07
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465455B1

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