4-Phenylbenzoyl chloride → N-(5-Chloropyridin-2-yl)-2-(4-phenylbenzoylamino)benzamide

HRID 1247039

Reaktionsgleichung

Reaktionsgleichung von HRID 1247039
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[N:6][CH:7]=1.[C:18]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:22][C:21]([C:24](Cl)=[O:25])=[CH:20][CH:19]=1>ClCCl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:24](=[O:25])[C:21]2[CH:22]=[CH:23][C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:19][CH:20]=2)=[N:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 841514-Phenylbenzoyl chlorideHCID 219063812-amino-N-(5-chloropyridin-2-yl)benzamide

Produkt 1

HCID 21906587N-(5-Chloropyridin-2-yl)-2-(4-phenylbenzoylamino)benzamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of N-(5-chloropyridin-2-yl)-2-aminobenzamide (0.247 g, 1 mmol) in dichloromethane (10 mL) and pyridine (0.5 mL) was added a solution of 4-biphenylcarbonyl chloride (0.217 g, 1 mmol) in dichloromethane (5 mL). After stirring overnight the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (50 mL) and water (25 mL). Separate the layers and wash the organic layer with water (2×10 mL), saturated sodium bicarbonate (2×20 mL), hydrochloric acid (0.2 N, 1×20 mL). Dried over MgSO4, filtered and concentrated in vacuo. The residue was then purified by RPHPLC (30% ethyl acetate/hexane) to give 0.4 g (94%) of pure product.

Aufarbeitung

  1. customwas removed in vacuo
  2. customThe residue was partitioned between ethyl acetate (50 mL) and water (25 mL)
  3. customSeparate the layers
  4. washwash the organic layer with water (2×10 mL), saturated sodium bicarbonate (2×20 mL), hydrochloric acid (0.2 N, 1×20 mL)
  5. dry with materialDried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by RPHPLC (30% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-198ee1f97c8c47cdb4df893751253757
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129245B2

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