2-Amino-5-chloropyridine → 4-chloro-N-(5-chloropyridin-2-yl)-3-nitrobenzamide

HRID 605212

Reaktionsgleichung

Reaktionsgleichung von HRID 605212
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=2)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Komponenten

5

Edukt 3

HCID 661742-Amino-5-chloropyridineHCID 81531DiisopropylethylamineHCID 1234774-Chloro-3-nitrobenzoyl chloride

Produkt 1

HCID 6930954-chloro-N-(5-chloropyridin-2-yl)-3-nitrobenzamideAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-3-nitrobenzoyl chloride (1.00 g, 4.99 mmol) in dry methylene chloride (20 mL) under a nitrogen atmosphere was treated with 2-amino-5-chloropyridine (643 mg, 4.99 mmol) and N,N-diisopropylethylamine (1.05 mL, 6.00 mmol), and the resulting mixture stirred at room temperature for 18 hours. The solvent was removed by rotary evaporation in vacuo, the residue taken up in ethyl acetate (100 mL), and washed with saturated aqueous sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL). The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Trituration with 5% ethyl acetate/methylene chloride afforded the title compound as a dark yellow solid (660 mg, 42%).

Aufarbeitung

  1. customThe solvent was removed by rotary evaporation in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d9fc8539c0fc4485a34f45d554db6fb9
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910595B2

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